N,N-Dimethylaniline → 4-Nitrobenzyl bromoacetate

HRID 569448Notes

Reaction equation

HRID 569448 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][OH:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].CN(C)C1C=CC=CC=1.[Br:21][CH2:22][C:23](Br)=[O:24]>C(OC(C)C)(C)C.C(OCC)C>[Br:21][CH2:22][C:23]([O:9][CH2:8][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:11][CH:10]=1)=[O:24]

Participants

6

Reactant 3

HCID 949N,N-DimethylanilineHCID 61147Bromoacetyl bromideHCID 692754-Nitrobenzyl alcohol

Product 1

HCID 70153214-Nitrobenzyl bromoacetate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 7914Diisopropyl EtherSolvent

Procedure

To a mixture of p-nitrobenzyl alcohol (45 g) and N,N-dimethylaniline (37.2 ml) in a mixture of diisopropyl ether and diethyl ether (300 ml) was added dropwise bromoacetyl bromide (25 ml) at 30° to 35° C., and the reaction mxture was stirred at the same temperature for an hour. After the reaction mixture was poured into ice-water, the separated organic layer was washed with 5% aqueous sodium bicarbonate. The solution was evaporated under reduced pressure to give p-nitrobenzyl bromoacetate. To a solution of this residue in N,N-dimethylformamide (150 ml) was added N-hydroxyphthalimide (39.3 g) and triethylamine (50 ml), and the reaction mixture was stirred for an hour at room temperature. The resultant mixture was poured into ice-water, and the precipitates were collected by filtration and washed with water to give p-nitrobenzyl 2-phthalimidooxyacetate (69.26 g).

Workup

  1. washthe separated organic layer was washed with 5% aqueous sodium bicarbonate
  2. customThe solution was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7a43a0caae9d43ccbde0eac068fed5d3
Source dataset
uspto-grants-1988_03
Patent number
US04731443

Reaction notes

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