Acetyl chloride → N-(4-bromo-2-fluorobenzyl)acetamide

HRID 859638Notes

Reaction equation

HRID 859638 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].C(N(CC)CC)C.Cl.[Br:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][NH2:19])=[C:16]([F:22])[CH:15]=1>C(Cl)Cl>[Br:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][NH:19][C:1](=[O:3])[CH3:2])=[C:16]([F:22])[CH:15]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 184681974-Bromo-2-fluorobenzylamine hydrochloride

Product 1

HCID 58764031N-(4-bromo-2-fluorobenzyl)acetamideYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (0.7 mL, 9.9 mmol) followed by triethylamine (2.8 mL, 19.9 mmol) were added to a suspension of 4-bromo-2-fluorobenzylamine hydrochloride (2 g, 8.3 mmol) in CH2Cl2 (20 mL). The mixture was stirred for 90 mins and then partitioned between 1 N HCl and EtOAc. The organic layers were brine, dried over Na2SO4 and concentrated. Purification by flash column chromatography (0% to 60% EtOAc in hexanes) gave the product as a clear oil (1.5 g, 74%). MS (ESI): 246.10, 248.10 (M+H)+

Workup

  1. custompartitioned between 1 N HCl and EtOAc
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customPurification by flash column chromatography (0% to 60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-39b6a809e45645c1875417ddd89b72df
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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