Benzoin → 2-Bromo-1,2-di-(4-chlorophenyl)ethanone

HRID 258998Notes

Reaction equation

HRID 258998 reaction equation
C1(C(C(C2C=CC=CC=2)O)=O)C=CC=CC=1.[Br:17]Br.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)=[O:27])=[CH:22][CH:21]=1>C(OCC)C>[Br:17][CH:28]([C:29]1[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=1)[C:26](=[O:27])[C:23]1[CH:24]=[CH:25][C:20]([Cl:19])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 8400BenzoinHCID 24408BromineHCID 5873181,2-Bis(4-chlorophenyl)ethanone

Product 1

HCID 112216182-Bromo-1,2-di-(4-chlorophenyl)ethanone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The benzoin starting material can be prepared by adding bromine (18.1g) dropwise to a stirred solution of 4,4'-dichlorodeoxybenzoin (30g) in dry diethylether (400ml). The solution is stirred for a further hour and evaporated to provide crude α-bromo-4,4'-dichlorodeoxybenzoin (40g) which when recrystallised from methanol has a melting point of 81°-83°.

Workup

  1. customevaporated

Sources & evidence

ORD record
ord-430831fadbfb44189894a8a63183ea83
Source dataset
uspto-grants-1977_07
Patent number
US04035499

Reaction notes

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