Bromine → 5-Bromo-2,3-bis(4-fluorophenyl)thiophene

HRID 280579Notes

Reaction equation

HRID 280579 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]([F:19])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[Br:20]Br>C(Cl)Cl.C(O)(=O)C>[Br:20][C:10]1[S:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[C:12]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH:11]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 11975814Thiophene, 2,3-bis(4-fluorophenyl)-

Product 1

HCID 131272535-Bromo-2,3-bis(4-fluorophenyl)thiopheneYield 83.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2,3-bis(4-fluorophenyl)thiophene (13.6 g, 50 mmole) in 120 ml methylene chloride and 150 ml acetic acid was cooled to ~5° and treated with bromine (2.8 ml, 55 mmole). After 4 hours, the reaction mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with saturated aqueous sodium bicarbonate and brine, dried and concentrated in vacuo. Recrystallization from ethanol gave the title compound (14.7 g), m.p. 91°-93°.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with saturated aqueous sodium bicarbonate and brine
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-977e61b7fa6042b49ca1e0a225e3f856
Source dataset
uspto-grants-1986_05
Patent number
US04590205

Reaction notes

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