Bromine → 5-Bromo-3-(4-fluorophenyl)-2-[4-(methylsulfanyl)phenyl]thiophene

HRID 620384Notes

Reaction equation

HRID 620384 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][S:10][C:9]=2[C:13]2[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[Br:21]Br>C(Cl)Cl.C(O)(=O)C>[Br:21][C:11]1[S:10][C:9]([C:13]2[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[CH:15][CH:14]=2)=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH:12]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 156173833-(4-Fluorophenyl)-2-[4-(methylsulfanyl)phenyl]thiophene

Product 1

HCID 136693245-Bromo-3-(4-fluorophenyl)-2-[4-(methylsulfanyl)phenyl]thiophene

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(4-fluorophenyl)-2-(4-methylthiophenyl)thiophene (15 g, 50 mmole) in methylene chloride (150 ml) was diluted with 150 ml of acetic acid and cooled to about 5°. A 1M solution of bromine in acetic acid (55 ml, 1.1 equiv.) was then added dropwise. The reaction mixture was stirred at 0° for 1.5 hours and then 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 (15.4 g), m.p. 113°-116°.

Workup

  1. temperaturecooled to about 5°
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthe solution washed with saturated aqueous sodium bicarbonate and brine
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-1579ab6fed034dddb2cb3dfa007f7ebb
Source dataset
uspto-grants-1989_04
Patent number
US04820827

Reaction notes

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