Benzohydroxamic acid → Benzeneacetic acid, 2-(bromomethyl)-, methyl ester
Reaction equation
C(NO)(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[C:17]1([CH3:28])[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][C:24]([O:26][CH3:27])=[O:25].[Br:29]N1C(=O)CCC1=O>C(#N)C>[Br:29][CH2:28][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][C:24]([O:26][CH3:27])=[O:25]Participants
6
Conditions
- Temperature
- 60 °C
Procedure
A mixture of 102 g (0.74 mol) of benzohydroxamic acid 2, 111 g (0.80 mol) of pulverised potassium carbonate and 1400 ml of acetonitrile is heated to 60° C. After 0.5 h, 162 g of methyl o-bromomethylphenylacetate 1, which is obtained as 68% crude product from the bromination of methyl o-tolylacetate with N-bromosuccinimide, dissolved in 100 ml of acetonitrile, is added dropwise over 0.5 h at 60° C.-65° C. and the reaction mixture is stirred for 5.5 h at this temperature.
Sources & evidence
- ORD record
- ord-2cd2d58c15bc48eab857a8e9c22036e3
- Source dataset
- uspto-grants-1997_02
- Patent number
- US05606095
Reaction notes
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