Thionyl Chloride → 2-(Chloromethyl)-1-benzothiophene

HRID 408562

Reaction equation

HRID 408562 reaction equation
[S:1]1[C:5]([CH2:6]O)=[CH:4][C:3]2[CH:8]=[CH:9][CH:10]=[CH:11][C:2]1=2.S(Cl)([Cl:14])=O>>[Cl:14][CH2:6][C:5]1[S:1][C:2]2[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=2[CH:4]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 27763352-(Hydroxymethyl)benzo[b]thiophene

Product 1

HCID 128138372-(Chloromethyl)-1-benzothiophene

Procedure

A solution of benzo[b]thiophen-2-yl-methanol (1 eq.) in thionyl chloride was stirred at 20° C. for 1 h. The crude was concentrated under reduced pressure then partitioned between a saturated aqueous solution of NaHCO3 and EtOAc. The organic layer was separated, dried over MgSO4, filtered and concentrated under reduced pressure to afford 2-chloromethyl-benzo[b]thiophene, used as such without further purification.

Workup

  1. concentrationThe crude was concentrated under reduced pressure
  2. customthen partitioned between a saturated aqueous solution of NaHCO3 and EtOAc
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3af8ca641c4b4f908efe1476df255b10
Source dataset
uspto-grants-2014_06
Patent number
US08759334B2

Linked notes

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