Bromoacetyl bromide → HCID 13944533, compound

HRID 987933Notes

Reaction equation

[CH2:1]([CH:8]1[CH2:12][O:11][C:10](=[O:13])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[Br:19][CH2:20][C:21](Br)=[O:22]>C1COCC1>[CH2:1]([CH:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:21](=[O:22])[CH2:20][Br:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 4-benzyl-2-oxazolidinone in dry THF (300 ml) was stirred at −78° C. under nitrogen during the dropwise addition of 1.6 M n-butyl lithium in hexanes, (60 ml, 97 mmol) followed by bromo-acetyl bromide. The pale yellow solution was stirred for a further 10 minutes at −78° C. and allowed to warm to room temperature over 30 minutes. The reaction was then quenched by the addition of saturated aqueous ammonium chloride solution. After dilution with ethyl acetate and brine, the two layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried (anhydrous magnesium sulfate) and concentrated in vacuo to give 4-benzyl-3-(2-bromo-acetyl)-oxazolidin-2-one (26.2 g) which was used in the next step without further purification.

Workup

temperatureto warm to room temperature over 30 minutes
customThe reaction was then quenched by the addition of saturated aqueous ammonium chloride solution
customAfter dilution with ethyl acetate and brine, the two layers were separated
extractionthe aqueous layer was extracted with ethyl acetate
washThe combined organic layers were washed with brine
dry with materialdried (anhydrous magnesium sulfate)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-ad2bb0613c444ab3b73792f2aed2293e
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06632826B1

Reaction notes

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