Thionyl Chloride → HCID 58566473, compound

HRID 445807Notes

Reaction equation

HRID 445807 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][C:6]1[S:10][C:9]2[C:11]([CH2:15]O)=[CH:12][CH:13]=[CH:14][C:8]=2[CH:7]=1>ClCCl>[Cl:3][CH2:15][C:11]1[C:9]2[S:10][C:6]([CH3:5])=[CH:7][C:8]=2[CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 58566649HCID 58566649, compound

Product 1

HCID 58566473HCID 58566473, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (0.415 mL, 5.69 mmol) was added slowly to an ice cold solution of the alcohol (510) (0.203 g, 1.14 mmol) in dichloromethane (6.0 mL). The reaction mixture was stirred and warmed to room temperature for 1 h. The resulting solution was quenched slowly with saturated sodium bicarbonate (10 mL) and extracted with dichloromethane, the organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to provide the intermediate 7-(chloromethyl)-2-methylbenzo[b]thiophene (511) (0.150 g, 67.0%) as a yellow oil.

Workup

  1. customThe resulting solution was quenched slowly with saturated sodium bicarbonate (10 mL)
  2. extractionextracted with dichloromethane
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6e38d76538f04dde9001aa6b6e3fb6c2
Source dataset
uspto-grants-2013_07
Patent number
US08476308B2

Reaction notes

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