Benzene → (2-Bromo-[1,1'-biphenyl)-3-yl)methyl acetate

HRID 1065583Notes

Reaction equation

HRID 1065583 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8](N)[C:7]=1[Br:13])(=[O:3])[CH3:2].N(OC(C)(C)C)=O.[CH:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[C:1]([O:4][CH2:5][C:6]1[C:7]([Br:13])=[C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:9]=[CH:10][CH:11]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 241BenzeneHCID 10906Tert-Butyl nitriteHCID 202706203-Amino-2-bromophenylmethyl acetate

Product 1

HCID 20270623(2-Bromo-[1,1'-biphenyl)-3-yl)methyl acetate

Procedure

A stirred solution of (3-amino-2-bromophenyl)methyl acetate (8.5 g, 0.035 mole) in 31.1 ml of benzene was heated at reflux. During a 40 minute period t-butyl nitrite (8.03 ml, 0.07 mole) was added to the reaction mixture. The mixture was refluxed for four hours, then held at room temperature for two days. The solvent was distilled from the reaction mixture under reduced pressure and 100 ml of n-heptane added to the residue. The solvent was removed by distillation under reduced pressure to give (2-bromo-[1,1'-biphenyl)-3-yl)methyl acetate (10.2 g) as an oil.

Workup

  1. temperatureat reflux
  2. temperatureThe mixture was refluxed for four hours
  3. distillationThe solvent was distilled from the reaction mixture under reduced pressure and 100 ml of n-heptane
  4. additionadded to the residue
  5. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-f1375621881145f2b641ac350e5a0bbe
Source dataset
uspto-grants-1982_05
Patent number
US04329518

Reaction notes

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