Dimethylamine → 2-(4-bromophenyl)-N,N-dimethylacetamide

HRID 1744092Notes

Reaction equation

HRID 1744092 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.C1[CH2:16][N:15]([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)[CH2:14]C1.F[P-](F)(F)(F)(F)F.CNC>CN(C=O)C.CCOCC>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([N:15]([CH3:16])[CH3:14])=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 674DimethylamineHCID 74654Benzeneacetic acid, 4-bromo-HCID 2724699PyBOP

Product 1

HCID 46315952-(4-bromophenyl)-N,N-dimethylacetamideYield 51.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4-bromophenylacetic acid (2.0 g, 9.3 mmol) and PyBOP (4.8 g, 9.3 mmol) in DMF (15 mL) was added dimethylamine (2 M solution in THF, 12 mL, 24 mmol). The solution was stirred overnight, then diluted with ether and washed with 1 M HCl, saturated aqueous NaHCO3 and brine to give 1.15 g 2-(4-bromophenyl)-N,N-dimethylacetamide.

Workup

  1. washwashed with 1 M HCl, saturated aqueous NaHCO3 and brine

Sources & evidence

ORD record
ord-1f8ea3b06303450eb827abb53f79a219
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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