Thionyl Chloride → 3-(Chloromethyl)-5-fluorobenzofuran
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]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
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
- 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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