1-chloro-2-phenylbenzene

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Bromochlorobenzene (96 mg, 0.50 mmol) reacted with phenylboronic acid (79 mg, 0.65 mmol) using 1/2 mol % of Pd(dba)2/Ph5FcP(t-Bu)2 and KF (87 mg, 1.50 mmol) in THF at room temperature to give the title compound (88 mg, 93%) as a white solid: 1H-NMR (400 MHz, CDCl3): δ 7.40-7.19 (m, 9H). 13C{1H}-NMR (100 MHz, CDCl3): δ 140.45, 139.33, 132.43, 131.32, 129.88, 129.39, 128.47, 127.99, 127.55, 126.77. GC/MS(EI):188 (M+), 190, 152, 76. at room temperature

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: When ethyl oxalyl chloride in the above example is replaced with methyl oxalyl chloride, propyl oxalyl chloride, i-propyl oxalyl chloride, t-butyl oxalyl chloride, or benzyl oxalyl chloride then the product obtained is methyl 2'-chloro-4-biphenylylglyoxylate, propyl 2'-chloro-4-biphenylylglyoxylate, i-propyl 2'-chloro-4-biphenylylglyoxoylate, t-butyl 2'-chloro-4-biphenylylglyoxylate, or benzyl 2'-chloro-4-biphenylylglyoxylate. the product obtained

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: When ethyl oxalyl chloride in the above example is replaced with methyl oxalyl chloride, propyl oxalyl chloride, i-propyl oxalyl chloride, t-butyl oxalyl chloride, or benzyl oxalyl chloride then the product obtained is methyl 2'-chloro-4-biphenylylglyoxylate, propyl 2'-chloro-4-biphenylylglyoxylate, i-propyl 2'-chloro-4-biphenylylglyoxoylate, t-butyl 2'-chloro-4-biphenylylglyoxylate, or benzyl 2'-chloro-4-biphenylylglyoxylate. the product obtained

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Bromochlorobenzene (96 mg, 0.50 mmol) reacted with phenylboronic acid (79 mg, 0.65 mmol) using 1/2 mol % of Pd(dba)2/Ph5FcP(t-Bu)2 and KF (87 mg, 1.50 mmol) in THF at room temperature to give the title compound (88 mg, 93%) as a white solid: 1H-NMR (400 MHz, CDCl3): δ 7.40-7.19 (m, 9H). 13C{1H}-NMR (100 MHz, CDCl3): δ 140.45, 139.33, 132.43, 131.32, 129.88, 129.39, 128.47, 127.99, 127.55, 126.77. GC/MS(EI):188 (M+), 190, 152, 76. at room temperature

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Bromochlorobenzene (96 mg, 0.50 mmol) reacted with phenylboronic acid (79 mg, 0.65 mmol) using 1/2 mol % of Pd(dba)2/Ph5FcP(t-Bu)2 and KF (87 mg, 1.50 mmol) in THF at room temperature to give the title compound (88 mg, 93%) as a white solid: 1H-NMR (400 MHz, CDCl3): δ 7.40-7.19 (m, 9H). 13C{1H}-NMR (100 MHz, CDCl3): δ 140.45, 139.33, 132.43, 131.32, 129.88, 129.39, 128.47, 127.99, 127.55, 126.77. GC/MS(EI):188 (M+), 190, 152, 76. at room temperature

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: When ethyl oxalyl chloride in the above example is replaced with methyl oxalyl chloride, propyl oxalyl chloride, i-propyl oxalyl chloride, t-butyl oxalyl chloride, or benzyl oxalyl chloride then the product obtained is methyl 2'-chloro-4-biphenylylglyoxylate, propyl 2'-chloro-4-biphenylylglyoxylate, i-propyl 2'-chloro-4-biphenylylglyoxoylate, t-butyl 2'-chloro-4-biphenylylglyoxylate, or benzyl 2'-chloro-4-biphenylylglyoxylate. the product obtained

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: It would be desirable to be able to prepare 4-chlorobiphenyl in a single step from biphenyl and chlorine. According to U.S. Pat. No. 1,890,427, this is possible by chlorination of biphenyl in chlorobenzene in the presence of metallic iron as catalyst. However, this gives a mixture comprising 4-chlorobiphenyl, 3-chlorobiphenyl, 2-chlorobiphenyl and unreacted biphenyl. The separation of this mixture is very complicated. For separating off one isomer, the reference describes crystallization from noneutectic mixtures above the freezing point of the eutectic. This means that separation of the entire mixture makes it necessary to carry out a complicated sequence of distillation and crystallization steps. Czech. Chem. Prum., 30(10), 529-32 (1980) confirms this. To achieve purities of greater than 99%, the latter reference describes the following steps to be carried out in succession for the separation of mixtures comprising 2-, 3- and 4-chlorobiphenyl: 1. distillation, 2. crystallization of the fractions from the distillation and 3. recrystallization of the fractions from the crystallization from ethanol.

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: It would be desirable to be able to prepare 4-chlorobiphenyl in a single step from biphenyl and chlorine. According to U.S. Pat. No. 1,890,427, this is possible by chlorination of biphenyl in chlorobenzene in the presence of metallic iron as catalyst. However, this gives a mixture comprising 4-chlorobiphenyl, 3-chlorobiphenyl, 2-chlorobiphenyl and unreacted biphenyl. The separation of this mixture is very complicated. For separating off one isomer, the reference describes crystallization from noneutectic mixtures above the freezing point of the eutectic. This means that separation of the entire mixture makes it necessary to carry out a complicated sequence of distillation and crystallization steps. Czech. Chem. Prum., 30(10), 529-32 (1980) confirms this. To achieve purities of greater than 99%, the latter reference describes the following steps to be carried out in succession for the separation of mixtures comprising 2-, 3- and 4-chlorobiphenyl: 1. distillation, 2. crystallization of the fractions from the distillation and 3. recrystallization of the fractions from the crystallization from ethanol.