No renderable structure data available
C1=CC(=C(C=C1C(=O)N)Br)OChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 3-bromo-4-hydroxybenzamide |
|---|---|
| IUPAC Name | — |
| CAS Number | 176979-22-9 |
| Database ID | 15169932 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
3-bromo-4-hydroxybenzamide (CAS 176979-22-9) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 15169932
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-8a44738f4c1e4d71bb4e65fc4252528eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 3-bromo-4-hydroxybenzoic acid (0.5 g) and DMF (0.1 ml) in DCM (10 ml) was added dropwise oxalyl chloride (0.6 ml). After stirring for 2 h, ammonia gas was purged through. After completion of reaction by tlc, the solvent was removed under reduced pressure. The residue was dissolved in water and extracted with ethyl acetate. The organics were dried over sodium sulphate and concentrated in vacuo to yield the title compound, 0.18 g ammonia gas was purged through After completion of reaction by tlc the solvent was removed under reduced pressure The residue was dissolved in water extracted with ethyl acetate The organics were dried over sodium sulphate concentrated in vacuo
Source ID: ord-a178908e21fb4633991d8699b7e0d472Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 3-bromo-4-hydroxybenzoic acid (0.5 g) and DMF (0.1 ml) in DCM (10 ml) was added dropwise oxalyl chloride (0.6 ml). After stirring for 2 h, ammonia gas was purged through. After completion of reaction by tlc, the solvent was removed under reduced pressure. The residue was dissolved in water and extracted with ethyl acetate. The organics were dried over sodium sulphate and concentrated in vacuo to yield the title compound, 0.18 g ammonia gas was purged through After completion of reaction by tlc the solvent was removed under reduced pressure The residue was dissolved in water extracted with ethyl acetate The organics were dried over sodium sulphate concentrated in vacuo
Source ID: ord-a178908e21fb4633991d8699b7e0d472Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Add K2CO3 (1.49 g, 10.8 mmol) to a solution of 4-fluorobenzaldehyde (1.16 mL, 10.8 mmol) and 3-bromo-4-hydroxy-benzamide (1.16 g, 5.4 mmol) in DMF (20 mL). Heat the mixture under N2 overnight. Cool the mixture at room temperature and pour it into ice-water. Extract the aqueous layer with EtOAc. Dry the organic layer over Na2SO4. Eliminate the solvent. Purify by flash chromatography (eluent: EtOAc/hexane 2/1 and 4/1) to get the title compound (1.0 g, 58%). 1H-NMR (metanol-d4, 300 MHz): 9.84 (s, 1H), 8.18 (d, 1H, J=2.0 Hz), 7.88-7.83 (m, 3H), 7.13 (d, 1H, J=8.5 Hz), 7.04-7.01 (m, 2H). Heat the mixture under N2 overnight Extract the aqueous layer with EtOAc Dry the organic layer over Na2SO4 Purify by flash chromatography (eluent: EtOAc/hexane 2/1 and 4/1)
Source ID: ord-1b8fa97c23064116a5b8f6a500936b7bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Add K2CO3 (1.49 g, 10.8 mmol) to a solution of 4-fluorobenzaldehyde (1.16 mL, 10.8 mmol) and 3-bromo-4-hydroxy-benzamide (1.16 g, 5.4 mmol) in DMF (20 mL). Heat the mixture under N2 overnight. Cool the mixture at room temperature and pour it into ice-water. Extract the aqueous layer with EtOAc. Dry the organic layer over Na2SO4. Eliminate the solvent. Purify by flash chromatography (eluent: EtOAc/hexane 2/1 and 4/1) to get the title compound (1.0 g, 58%). 1H-NMR (metanol-d4, 300 MHz): 9.84 (s, 1H), 8.18 (d, 1H, J=2.0 Hz), 7.88-7.83 (m, 3H), 7.13 (d, 1H, J=8.5 Hz), 7.04-7.01 (m, 2H). Heat the mixture under N2 overnight Extract the aqueous layer with EtOAc Dry the organic layer over Na2SO4 Purify by flash chromatography (eluent: EtOAc/hexane 2/1 and 4/1)
Source ID: ord-1b8fa97c23064116a5b8f6a500936b7bConditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-Bromo-4-hydroxy-benzonitrile (495 mg, 2.5 mmol) is dissolved in H2SO4 98%, heat the solution at 80° C. for 1 hour. Cool the mixture at room temperature and pour it into ice-water. Extract the aqueous layer with EtOAc. Dry the organic layer over Na2SO4. Eliminate the solvent to obtain the title compound (450 mg, 83%). 1H-NMR (metanol-d4, 200 MHz): 8.04 (d, 1H, J=2.0 Hz), 7.70 (dd, 1H, J=2.0 and 8.4 Hz), 6.93 (d, 1H, J=8.6 Hz) Cool the mixture at room temperature Extract the aqueous layer with EtOAc Dry the organic layer over Na2SO4
Source ID: ord-37989e744f4247bc9b48a95c7f45fb23Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Add K2CO3 (1.49 g, 10.8 mmol) to a solution of 4-fluorobenzaldehyde (1.16 mL, 10.8 mmol) and 3-bromo-4-hydroxy-benzamide (1.16 g, 5.4 mmol) in DMF (20 mL). Heat the mixture under N2 overnight. Cool the mixture at room temperature and pour it into ice-water. Extract the aqueous layer with EtOAc. Dry the organic layer over Na2SO4. Eliminate the solvent. Purify by flash chromatography (eluent: EtOAc/hexane 2/1 and 4/1) to get the title compound (1.0 g, 58%). 1H-NMR (metanol-d4, 300 MHz): 9.84 (s, 1H), 8.18 (d, 1H, J=2.0 Hz), 7.88-7.83 (m, 3H), 7.13 (d, 1H, J=8.5 Hz), 7.04-7.01 (m, 2H). Heat the mixture under N2 overnight Extract the aqueous layer with EtOAc Dry the organic layer over Na2SO4 Purify by flash chromatography (eluent: EtOAc/hexane 2/1 and 4/1)
Source ID: ord-d7d8e0afdf274526b753e76387673f38Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-Bromo-4-hydroxy-benzonitrile (495 mg, 2.5 mmol) is dissolved in H2SO4 98%, heat the solution at 80° C. for 1 hour. Cool the mixture at room temperature and pour it into ice-water. Extract the aqueous layer with EtOAc. Dry the organic layer over Na2SO4. Eliminate the solvent to obtain the title compound (450 mg, 83%). 1H-NMR (metanol-d4, 200 MHz): 8.04 (d, 1H, J=2.0 Hz), 7.70 (dd, 1H, J=2.0 and 8.4 Hz), 6.93 (d, 1H, J=8.6 Hz) Cool the mixture at room temperature Extract the aqueous layer with EtOAc Dry the organic layer over Na2SO4
Source ID: ord-6bcd3c0f6b7f4f56ab4d24db404d32c0Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Add K2CO3 (1.49 g, 10.8 mmol) to a solution of 4-fluorobenzaldehyde (1.16 mL, 10.8 mmol) and 3-bromo-4-hydroxy-benzamide (1.16 g, 5.4 mmol) in DMF (20 mL). Heat the mixture under N2 overnight. Cool the mixture at room temperature and pour it into ice-water. Extract the aqueous layer with EtOAc. Dry the organic layer over Na2SO4. Eliminate the solvent. Purify by flash chromatography (eluent: EtOAc/hexane 2/1 and 4/1) to get the title compound (1.0 g, 58%). 1H-NMR (metanol-d4, 300 MHz): 9.84 (s, 1H), 8.18 (d, 1H, J=2.0 Hz), 7.88-7.83 (m, 3H), 7.13 (d, 1H, J=8.5 Hz), 7.04-7.01 (m, 2H). Heat the mixture under N2 overnight Extract the aqueous layer with EtOAc Dry the organic layer over Na2SO4 Purify by flash chromatography (eluent: EtOAc/hexane 2/1 and 4/1)
Source ID: ord-86f06c716e9747b6b357085c599302e3Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-Bromo-4-hydroxy-benzonitrile (495 mg, 2.5 mmol) is dissolved in H2SO4 98%, heat the solution at 80° C. for 1 hour. Cool the mixture at room temperature and pour it into ice-water. Extract the aqueous layer with EtOAc. Dry the organic layer over Na2SO4. Eliminate the solvent to obtain the title compound (450 mg, 83%). 1H-NMR (metanol-d4, 200 MHz): 8.04 (d, 1H, J=2.0 Hz), 7.70 (dd, 1H, J=2.0 and 8.4 Hz), 6.93 (d, 1H, J=8.6 Hz) Cool the mixture at room temperature Extract the aqueous layer with EtOAc Dry the organic layer over Na2SO4
Source ID: ord-72cd4c6ae79144deb8de692b6ff3ff36Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 3-bromo-4-hydroxybenzoic acid (0.5 g) and DMF (0.1 ml) in DCM (10 ml) was added dropwise oxalyl chloride (0.6 ml). After stirring for 2 h, ammonia gas was purged through. After completion of reaction by tlc, the solvent was removed under reduced pressure. The residue was dissolved in water and extracted with ethyl acetate. The organics were dried over sodium sulphate and concentrated in vacuo to yield the title compound, 0.18 g ammonia gas was purged through After completion of reaction by tlc the solvent was removed under reduced pressure The residue was dissolved in water extracted with ethyl acetate The organics were dried over sodium sulphate concentrated in vacuo
Source ID: ord-0753a99e195a453d8e41f72e91d9408aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Add K2CO3 (1.49 g, 10.8 mmol) to a solution of 4-fluorobenzaldehyde (1.16 mL, 10.8 mmol) and 3-bromo-4-hydroxy-benzamide (1.16 g, 5.4 mmol) in DMF (20 mL). Heat the mixture under N2 overnight. Cool the mixture at room temperature and pour it into ice-water. Extract the aqueous layer with EtOAc. Dry the organic layer over Na2SO4. Eliminate the solvent. Purify by flash chromatography (eluent: EtOAc/hexane 2/1 and 4/1) to get the title compound (1.0 g, 58%). 1H-NMR (metanol-d4, 300 MHz): 9.84 (s, 1H), 8.18 (d, 1H, J=2.0 Hz), 7.88-7.83 (m, 3H), 7.13 (d, 1H, J=8.5 Hz), 7.04-7.01 (m, 2H). Heat the mixture under N2 overnight Extract the aqueous layer with EtOAc Dry the organic layer over Na2SO4 Purify by flash chromatography (eluent: EtOAc/hexane 2/1 and 4/1)
Source ID: ord-d7d8e0afdf274526b753e76387673f38PubChem References
These sources are listed in the compound's public database record.
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