Water → alpha-(2-Nitrophenyl)-p-bromocinnamic acid

HRID 1646047Notes

Reaction equation

HRID 1646047 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[N+:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][C:20]([OH:22])=[O:21])([O-:12])=[O:11].C(N(CC)CC)C.O>C(OC(=O)C)(=O)C>[N+:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19](=[CH:6][C:5]1[CH:8]=[CH:9][C:2]([Br:1])=[CH:3][CH:4]=1)[C:20]([OH:22])=[O:21])([O-:12])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 707414-BromobenzaldehydeHCID 77337(2-Nitrophenyl)acetic acid

Product 1

HCID 54296204alpha-(2-Nitrophenyl)-p-bromocinnamic acidYield 92.5%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 4-bromobenzaldehyde (27.75 g, 0.150 mol), 2-nitrophenylacetic acid (27.18 g, 0.150 mol) and triethylamine (21.0 ml, 0.150 mol) in 150 ml of acetic anhydride was heated at 40° C. for 38 hours and then poured into 900 ml of water and stirred until the organic layer solidified. The solid was isolated by filtration and dried in vacuo to yield 48.3 g (92%) of the title compound as a tan solid which was sufficiently pure to use directly in the next reaction.

Workup

  1. customThe solid was isolated by filtration
  2. customdried in vacuo

Sources & evidence

ORD record
ord-9158f74af1e94838b4ac435ba9e5092f
Source dataset
uspto-grants-1993_01
Patent number
US05177202

Reaction notes

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