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

HRID 620386Notes

Reaction equation

HRID 620386 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][CH3:20])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[Br:21]Br>C(Cl)Cl.C(O)(=O)C>[Br:21][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][CH3:20])=[CH:15][CH:14]=2)[CH:11]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 105903572-(4-fluorophenyl)-3-(4-methylsulfanylphenyl)thiophene

Product 1

HCID 136693225-Bromo-2-(4-fluorophenyl)-3-[4-(methylsulfanyl)phenyl]thiophene

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(4-fluorophenyl)-3-(4-methylthiophenyl)thiophene (7.5 g, 25 mmole) in methylene chloride (75 ml) was diluted with 75 ml of acetic acid, cooled to about 5°, and treated dropwise with a 1M solution of bromine in acetic acid (28 ml, 1.1 equiv). The reaction mixture was stirred at 5° 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 evaporated. Recrystallization from methanol, with cooling in Dry Ice, gave the title compound in two crops (7.60 g), m.p. 75°-78°. Infrared and NMR spectral data were consistent with the assigned structure.

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. customevaporated
  7. customRecrystallization from methanol
  8. temperaturewith cooling in Dry Ice

Sources & evidence

ORD record
ord-099a2d97a6ef47ed8b978fdc6ebac6ca
Source dataset
uspto-grants-1989_04
Patent number
US04820827

Reaction notes

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