Bromoacetyl bromide → N-(Benzyloxy)-2-bromoacetamide

HRID 392017Notes

Reaction equation

HRID 392017 reaction equation
Cl.[CH2:2]([O:9][NH2:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:11][CH2:12][C:13](Br)=[O:14].C(N(C(C)C)CC)(C)C>C1COCC1.C(OCC)(=O)C.O>[Br:11][CH2:12][C:13]([NH:10][O:9][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[O:14]

Participants

7

Reactant 3

HCID 61147Bromoacetyl bromideHCID 81531DiisopropylethylamineHCID 102312Benzyloxyamine hydrochloride

Product 1

HCID 15434886N-(Benzyloxy)-2-bromoacetamideYield 52%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of O-benzylhydroxylamine hydrochloride (1.6 g, 10 mmol) in THF (40 mL) at 0° C., was added bromoacetyl bromide (871 μL, 10 mmol) and diisopropylethylamine (3.5 mL, 20 mmol). The reaction mixture was warmed to room temperature overnight and diluted with ethyl acetate and water. The aqueous layer was separated and extracted with ethyl acetate. The organic layers were combined, dried over Na2SO4, filtered and concentrated in vacuo. The crude material was purified by silica gel flash column chromatography with ethyl acetate-hexane to give 1.27 g (52%) of the title compound.

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by silica gel flash column chromatography with ethyl acetate-hexane

Sources & evidence

ORD record
ord-c59f5fdcef034299952d15cbb83993a9
Source dataset
uspto-grants-2004_10
Patent number
US06800444B1

Reaction notes

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