Water → HCID 2109349, compound

HRID 2358962Notes

Reaction equation

HRID 2358962 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1.[C:10]([O:13][CH2:14][C:15](Cl)=[O:16])(=[O:12])[CH3:11].O>C(Cl)(Cl)Cl>[C:10]([O:13][CH2:14][C:15]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([Br:1])=[CH:3][C:4]=1[F:9])=[O:16])(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 962WaterHCID 26297Acetoxyacetyl chlorideHCID 1230504-Bromo-2-fluoroaniline

Product 1

HCID 2109349HCID 2109349, compoundYield 104.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 4-bromo-2-fluoroaniline (9.5 g, 50.0 mmol) in 150 ml dry CHCl3 was added drop wise acetoxyacetyl chloride (7.5 g, 55.0 mmol) under nitrogen. The mixture was stirred at room temperature for 0.5 h, then water was added and the solution was extracted several times with dichloromethane. The combined organic layers were washed with brine, dried over MgSO4 and evaporated, affording 2-(4-bromo-2-fluorophenylamino)-2-oxoethyl acetate (15.2 g) as colorless solid in quantitative yield.

Workup

  1. extractionthe solution was extracted several times with dichloromethane
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-dfe7e44d8abd4bbdb8b0bbcffca6e0c1
Source dataset
uspto-grants-2014_04
Patent number
US08685960B2

Reaction notes

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