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COC1=C(C=CC(=C1)CC#N)ClChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 2-(4-chloro-3-methoxyphenyl)acetonitrile |
|---|---|
| IUPAC Name | — |
| CAS Number | 13726-21-1 |
| Database ID | 20460956 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
2-(4-chloro-3-methoxyphenyl)acetonitrile (CAS 13726-21-1) 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 20460956
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-748279f21f064ca9a5f9ac895e41614cConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-7e195b5c9be24ba5b1cc1a045523df48Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: BBr3 (16.6 g, 66 mmol) was slowly added to a solution of 2-(4-chloro-3-methoxyphenyl)acetonitrile (12 g, 66 mmol) in DCM (120 mL) at −78° C. under N2. The reaction temperature was slowly increased to room temperature. The reaction mixture was stirred overnight and then poured into ice and water. The organic layer was separated, and the aqueous layer was extracted with DCM (40 mL×3). The combined organic layers were washed with water, brine, dried over Na2SO4, and concentrated under vacuum to give (4-chloro-3-hydroxy-phenyl)-acetonitrile (9.3 g, 85%). 1H NMR (300 MHz, CDCl3) δ 7.34 (d, J=8.4 Hz, 1H), 7.02 (d, J=2.1 Hz, 1H), 6.87 (dd, J=2.1, 8.4 Hz, 1H), 5.15 (brs, 1H), 3.72 (s, 2H). The organic layer was separated the aqueous layer was extracted with DCM (40 mL×3) The combined organic layers were washed with water, brine dried over Na2SO4 concentrated under vacuum
Source ID: ord-8a189023d76048529b46b6e0df9f0999Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: BBr3 (16.6 g, 66 mmol) was slowly added to a solution of 2-(4-chloro-3-methoxyphenyl)acetonitrile (12 g, 66 mmol) in DCM (120 mL) at −78° C. under N2. The reaction temperature was slowly increased to room temperature. The reaction mixture was stirred overnight and then poured into ice-water. The organic layer was separated and the aqueous layer was extracted with DCM (40 mL×3). The combined organic layers were washed with water, brine, dried over Na2SO4, and concentrated under vacuum to give (4-chloro-3-hydroxy-phenyl)-acetonitrile (9.3 g, 85%). 1H NMR (300 MHz, CDCl3) δ 7.34 (d, J=8.4 Hz, 1H), 7.02 (d, J=2.1 Hz, 1H), 6.87 (dd, J=2.1, 8.4 Hz, 1H), 5.15 (brs, 1H), 3.72 (s, 2H). The organic layer was separated the aqueous layer was extracted with DCM (40 mL×3) The combined organic layers were washed with water, brine dried over Na2SO4 concentrated under vacuum
Source ID: ord-a802c3d657ef4a0eb4d56fc5941ee5beConditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 4-bromomethyl-1-chloro-2-methoxy-benzene (68.5 g, 0.29 mol) in C2H5OH (90%, 500 mL) was added NaCN (28.5 g, 0.58 mol). The mixture was stirred at 60° C. overnight. Ethanol was evaporated and the residue was dissolved in H2O. The mixture was extracted with ethyl acetate (300 mL×3). The combined organic layers were washed with brine, dried over Na2SO4 and purified by column chromatography on silica gel (Petroleum Ether/EtOAc 30:1) to give 2-(4-chloro-3-methoxyphenyl)acetonitrile (25 g, 48%). 1H NMR (400 MHz, CDCl3) δ 7.36 (d, J=8 Hz, 1H), 6.88-6.84 (m, 2H), 3.92 (s, 3H), 3.74 (s, 2H). 13C NMR (100 MHz, CDCl3) δ 155.4, 130.8, 129.7, 122.4, 120.7, 117.5, 111.5, 56.2, 23.5. Ethanol was evaporated the residue was dissolved in H2O The mixture was extracted with ethyl acetate (300 mL×3) The combined organic layers were washed with brine dried over Na2SO4 purified by column chromatography on silica gel (Petroleum Ether/EtOAc 30:1)
Source ID: ord-c8993b612f6f42ef8e2ad537b60fccbaConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-748279f21f064ca9a5f9ac895e41614cConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-7e195b5c9be24ba5b1cc1a045523df48Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: BBr3 (16.6 g, 66 mmol) was slowly added to a solution of 2-(4-chloro-3-methoxyphenyl)acetonitrile (12 g, 66 mmol) in DCM (120 mL) at −78° C. under N2. The reaction temperature was slowly increased to room temperature. The reaction mixture was stirred overnight and then poured into ice and water. The organic layer was separated, and the aqueous layer was extracted with DCM (40 mL×3). The combined organic layers were washed with water, brine, dried over Na2SO4, and concentrated under vacuum to give (4-chloro-3-hydroxy-phenyl)-acetonitrile (9.3 g, 85%). 1H NMR (300 MHz, CDCl3) δ 7.34 (d, J=8.4 Hz, 1 H), 7.02 (d, J=2.1 Hz, 1 H), 6.87 (dd, J=2.1, 8.4 Hz, 1 H), 5.15 (brs, 1 H), 3.72 (s, 2 H). The organic layer was separated the aqueous layer was extracted with DCM (40 mL×3) The combined organic layers were washed with water, brine dried over Na2SO4 concentrated under vacuum
Source ID: ord-c21e0d03125d48fa89d92da122d415e6Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: BBr3 (16.6 g, 66 mmol) was slowly added to a solution of 2-(4-chloro-3-methoxyphenyl)acetonitrile (12 g, 66 mmol) in DCM (120 mL) at −78° C. under N2. The reaction temperature was slowly increased to room temperature. The reaction mixture was stirred overnight and then poured into ice and water. The organic layer was separated, and the aqueous layer was extracted with DCM (40 mL×3). The combined organic layers were washed with water, brine, dried over Na2SO4, and concentrated under vacuum to give (4-chloro-3-hydroxy-phenyl)-acetonitrile (9.3 g, 85%). 1H NMR (300 MHz, CDCl3) δ 7.34 (d, J=8.4 Hz, 1 H), 7.02 (d, J=2.1 Hz, 1 H), 6.87 (dd, J=2.1, 8.4 Hz, 1 H), 5.15 (brs, 1 H), 3.72 (s, 2 H). The organic layer was separated the aqueous layer was extracted with DCM (40 mL×3) The combined organic layers were washed with water, brine dried over Na2SO4 concentrated under vacuum
Source ID: ord-c21e0d03125d48fa89d92da122d415e6Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: BBr3 (16.6 g, 66 mmol) was slowly added to a solution of 2-(4-chloro-3-methoxyphenyl)acetonitrile (12 g, 66 mmol) in DCM (120 mL) at −78° C. under N2. The reaction temperature was slowly increased to room temperature. The reaction mixture was stirred overnight and then poured into ice-water. The organic layer was separated and the aqueous layer was extracted with DCM (40 mL×3). The combined organic layers were washed with water, brine, dried over Na2SO4, and concentrated under vacuum to give (4-chloro-3-hydroxy-phenyl)-acetonitrile (9.3 g, 85%). 1H NMR (300 MHz, CDCl3) δ 7.34 (d, J=8.4 Hz, 1 H), 7.02 (d, J=2.1 Hz, 1 H), 6.87 (dd, J=2.1, 8.4 Hz, 1 H), 5.15 (brs, 1H), 3.72 (s, 2 H). The organic layer was separated the aqueous layer was extracted with DCM (40 mL×3) The combined organic layers were washed with water, brine dried over Na2SO4 concentrated under vacuum
Source ID: ord-461a0ec7a2d040b8b37e6fd58cda902dConditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 4-bromomethyl-1-chloro-2-methoxy-benzene (68.5 g, 0.29 mol) in C2H5OH (90%, 500 mL) was added NaCN (28.5 g, 0.58 mol). The mixture was stirred at 60° C. overnight. Ethanol was evaporated and the residue was dissolved in H2O. The mixture was extracted with ethyl acetate (300 mL×3). The combined organic layers were washed with brine, dried over Na2SO4 and purified by column chromatography on silica gel (Petroleum Ether/EtOAc 30:1) to give 2-(4-chloro-3-methoxyphenyl)acetonitrile (25 g, 48%). 1H NMR (400 MHz, CDCl3) δ 7.36 (d, J=8 Hz, 1 H), 6.88-6.84 (m, 2 H), 3.92 (s, 3 H), 3.74 (s, 2 H). 13c NMR (100 MHz, CDCl3) δ 155.4, 130.8, 129.7, 122.4, 120.7, 117.5, 111.5, 56.2, 23.5. Ethanol was evaporated the residue was dissolved in H2O The mixture was extracted with ethyl acetate (300 mL×3) The combined organic layers were washed with brine dried over Na2SO4 purified by column chromatography on silica gel (Petroleum Ether/EtOAc 30:1)
Source ID: ord-84b9927654834cb8b5e901ae23497c39Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: BBr3 (16.6 g, 66 mmol) was slowly added to a solution of 2-(4-chloro-3-methoxyphenyl)acetonitrile (12 g, 66 mmol) in DCM (120 mL) at −78° C. under N2. The reaction temperature was slowly increased to room temperature. The reaction mixture was stirred overnight and then poured into ice and water. The organic layer was separated, and the aqueous layer was extracted with DCM (40 mL×3). The combined organic layers were washed with water, brine, dried over Na2SO4, and concentrated under vacuum to give (4-chloro-3-hydroxy-phenyl)-acetonitrile (9.3 g, 85%). 1H NMR (300 MHz, CDCl3) δ 7.34 (d, J=8.4 Hz, 1 H), 7.02 (d, J=2.1 Hz, 1 H), 6.87 (dd, J=2.1, 8.4 Hz, 1 H), 5.15 (brs, 1H), 3.72 (s, 2 H). The organic layer was separated the aqueous layer was extracted with DCM (40 mL×3) The combined organic layers were washed with water, brine dried over Na2SO4 concentrated under vacuum
Source ID: ord-eea333b1adb84c358065334325a1205bPubChem References
These sources are listed in the compound's public database record.
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