Thionyl Chloride → HCID 58566473, compound

HRID 2069609Notes

Reaction equation

HRID 2069609 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-eb154498e4914898a0f32ee16bd36c6d
Source dataset
uspto-grants-2012_10
Patent number
US08299117B2

Reaction notes

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