Thionyl Chloride → 3-(Chloromethyl)-5-fluorobenzofuran

HRID 1358239Notes

Reaction equation

HRID 1358239 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[C:7]([CH2:10]O)[C:6]=2[CH:12]=1.S(Cl)([Cl:15])=O>C(Cl)Cl.CN(C)C=O>[Cl:15][CH2:10][C:7]1[C:6]2[CH:12]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[O:9][CH:8]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 18184309HCID 18184309, compound

Product 1

HCID 181843143-(Chloromethyl)-5-fluorobenzofuran

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 5-fluorobenzofuran-3-ylmethanol (14 g) in methylene chloride (250 mL) was treated successively with 5 drops of dimethylformamide and thionyl chloride (28 mL). After stirring for 16 h at room temperature the reaction was concentrated in vacuo giving 3-chloromethyl-5-fluorobenzofuran as an oil (19.4 g).

Workup

  1. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-85b6230b51dd41d899267ece7db4995d
Source dataset
uspto-grants-2003_07
Patent number
US06596722B2

Reaction notes

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