Bromine → 3'-(2-Bromoacetyl)-4'-fluoromethanesulfonanilide

HRID 2379183Notes

Reaction equation

HRID 2379183 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][C:14]=1[F:15])[NH:7][S:8]([CH3:11])(=[O:10])=[O:9])(=[O:3])[CH3:2].[Br:16]Br>C(O)(=O)C>[Br:16][CH2:2][C:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][C:14]=1[F:15])[NH:7][S:8]([CH3:11])(=[O:10])=[O:9])=[O:3]

Participants

4

Reactant 2

HCID 24408BromineHCID 111071753'-Acetyl-4'-fluoromethanesulfonanilide

Product 1

HCID 221413933'-(2-Bromoacetyl)-4'-fluoromethanesulfonanilideYield 88.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3'-Acetyl-4'-fluoromethanesulfonanilide (32 g) was dissolved in 250 ml of acetic acid, then 22.1 g of bromine was dropped thereinto gradually at room temperature and the mixture was made to react at room temperature for 3 hours. The reaction mixture was added to ice water and the mixture-was extracted with ethyl acetate. The extract was washed with aqueous solution of sodium bicarbonate, then with water, dried and the solvent was evaporated therefrom followed by crystallizing from diisopropyl ether to give 38 g of 3'-(2-bromoacetyl)-4'-fluoromethanesulfonanilide, m.p. 110°-113° C.

Workup

  1. customgradually at room temperature
  2. customto react at room temperature for 3 hours
  3. extractionthe mixture-was extracted with ethyl acetate
  4. washThe extract was washed with aqueous solution of sodium bicarbonate
  5. dry with materialwith water, dried
  6. customthe solvent was evaporated
  7. customby crystallizing from diisopropyl ether

Sources & evidence

ORD record
ord-7bc91113b29840a0856437345ad235fd
Source dataset
uspto-grants-1994_11
Patent number
US05360822

Reaction notes

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