Bromine → HCID 18615210, compound

HRID 1955797Notes

Reaction equation

HRID 1955797 reaction equation
CC(O)=O.C1COCC1.[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:19])[CH3:18])=[CH:13][C:12]=1[NH:20][S:21]([CH3:24])(=[O:23])=[O:22].[Br:25]Br>CCOC(C)=O.CCCCCC>[Br:25][CH2:18][C:17]([C:14]1[CH:15]=[CH:16][C:11]([F:10])=[C:12]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH:13]=1)=[O:19]

Participants

5

Reactant 3

HCID 24408Bromine2×HCID 18615111HCID 18615111, compoundHCID 23444217Acetic acid tetrahydrofuran

Product 1

HCID 18615210HCID 18615210, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a stirred 20° C. solution (4 mL) of 40% HOAc/THF containing 1-[4-fluoro-3-[(methylsulfonyl)amino]phenyl]ethanone (1.0 g, 4.3 mmol) was added bromine (223 mL, 4.3 mmol). After stirring one hour, a second equivalent of bromine was added and the reaction run for 3.5 hours whereupon the reaction was judged complete by TLC (1:1 EtOAc/hexane). After dilution with EtOAc, the organic layer was washed with aq. NaHCO3 and then brine before drying over Na2SO4. After concentration, 0.58 g (44%) of the title compound was isolated after recrystallization from EtOH.

Workup

  1. washAfter dilution with EtOAc, the organic layer was washed with aq. NaHCO3
  2. dry with materialbrine before drying over Na2SO4
  3. concentrationAfter concentration

Sources & evidence

ORD record
ord-fc15bfca902b4ac6a4140ba63382a72a
Source dataset
uspto-grants-1998_07
Patent number
US05776983

Reaction notes

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