Thionyl Chloride → 2-((5-Bromo-2-fluorophenyl)chloromethyl)benzo(b)thiophene

HRID 218982Notes

Reaction equation

HRID 218982 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH:10]([C:12]1[CH:17]=[C:16]([Br:18])[CH:15]=[CH:14][C:13]=1[F:19])O.S(Cl)([Cl:22])=O>C(#N)C>[Br:18][C:16]1[CH:15]=[CH:14][C:13]([F:19])=[C:12]([CH:10]([Cl:22])[C:2]2[S:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[CH:3]=2)[CH:17]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 59281673Benzo[b]thiophen-2-yl(5-bromo-2-fluorophenyl)methanol

Product 1

HCID 249881712-((5-Bromo-2-fluorophenyl)chloromethyl)benzo(b)thiopheneYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
15 °C

Procedure

Into an acetonitrile (10 ml) solution of 1-benzothien-2-yl(5-bromo-2-fluorophenyl)methanol (1.0 g) was dropwise added thionyl chloride (706 mg) at a temperature of 5° C. or lower, followed by stirring at 5.0 to 25.0° C. for 3.5 hours. The reaction mixture was subjected to distillation under reduced pressure to distill off the solvent and the residue was subjected to vacuum drying to obtain 2-[(5-bromo-2-fluorophenyl)(chloro)methyl]-1-benzothiophene [1.05 g, yield: 100%, purity: 99% (HPLC)].

Workup

  1. customat a temperature of 5° C.
  2. distillationThe reaction mixture was subjected to distillation under reduced pressure
  3. distillationto distill off the solvent
  4. customdrying

Sources & evidence

ORD record
ord-42541e997b2d44188611f7af946bb8a6
Source dataset
uspto-grants-2012_06
Patent number
US08198464B2

Reaction notes

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