Bromine → 5-Bromo-2-(4-fluorophenyl)-3-(4-(methylsulfonyl)phenyl)thiophene

HRID 620385Notes

Reaction equation

HRID 620385 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[CH:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[Br:23]Br>C(Cl)Cl.C(O)(=O)C>[Br:23][C:10]1[S:9][C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[C:12]([C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)[CH:11]=1

Participants

5

Reactant 2

HCID 24408Bromine2×HCID 103368732-(4-Fluorophenyl)-3-(4-methylsulfonylphenyl)thiophene

Product 1

HCID 31775-Bromo-2-(4-fluorophenyl)-3-(4-(methylsulfonyl)phenyl)thiophene

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of the crude 2-(4-fluorophenyl)-3-(4-methylsulfonylphenyl)thiophene of Example 2a (12.6 g, up to 30 mmole) in methylene chloride (100 ml) was diluted with 75 ml of acetic acid and cooled to about 5°. A 1M solution of bromine in acetic acid (33 ml, 1.1 equiv) was added and the reaction stirred at about 5°. After 1 hour, additional bromine solution (5 ml) was added. After 2 hours total reaction time, the reaction mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate and the solution washed with saturated aqueous sodium bicarbonate and brine, dried, and concentrated in vacuo. Recrystallization from ethanol gave the title compound (7.9 g), m.p. 122°-124°. Infrared and NMR spectral data were consistent with the assigned structure.

Workup

  1. temperaturecooled to about 5°
  2. waitAfter 2 hours total reaction time
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washthe solution washed with saturated aqueous sodium bicarbonate and brine
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-a8c69f156b774798b8f07baae6e2f520
Source dataset
uspto-grants-1989_04
Patent number
US04820827

Reaction notes

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