Thionyl Chloride → 2-(Chloromethyl)-3-methylbenzo[b]thiophene

HRID 241358Notes

Reaction equation

HRID 241358 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:4][C:3]=1[CH2:11]O.S(Cl)([Cl:15])=O>C1C=CC=CC=1>[Cl:15][CH2:11][C:3]1[S:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 6012933-Methylbenzo(b)thiophene-2-methanol

Product 1

HCID 132472182-(Chloromethyl)-3-methylbenzo[b]thiopheneYield 103.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To an ice-cold solution of 3-methylbenzothiophene-2-methanol [Reference example 1] (480 mg, 2.69 mmol) in benzene (10 mL) was added dropwise, a solution of thionyl chloride (0.24 mL, 3.2 mmol) in benzene (3.5 mL). The mixture was stirred at room temperature for 3 hour, and concentrated under reduced pressure to give 2-chloromethyl-3-methylbenzothiophene as a yellow oil (548 mg, yield>99%).

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a7404733637740e88021877d174956ad
Source dataset
uspto-grants-2014_02
Patent number
US08648208B2

Reaction notes

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