Thionyl Chloride → HCID 13663048, compound

HRID 280601Notes

Reaction equation

HRID 280601 reaction equation
S(Cl)([Cl:3])=O.[Br:5][C:6]1[CH:7]=[CH:8][C:9]2[C:13]([CH3:14])=[C:12]([CH2:15]O)[S:11][C:10]=2[CH:17]=1>N1C=CC=CC=1.C(Cl)(Cl)Cl>[Br:5][C:6]1[CH:7]=[CH:8][C:9]2[C:13]([CH3:14])=[C:12]([CH2:15][Cl:3])[S:11][C:10]=2[CH:17]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 13663046HCID 13663046, compound

Product 1

HCID 13663048HCID 13663048, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6212ChloroformSolvent

Procedure

Thionyl chloride (2.0 ml) was added dropwise to a stirred solution of 6-bromo-2-hydroxymethyl-3-methylbenzo[b]thiophene (3.60 g) and pyridine (3 drops) in chloroform (80 ml). The solution was stirred at room temperature for 1 hour, then washed with water, sodium bicarbonate solution and dried (Na2SO4). Evaporation of the solvent gave a quantitative yield of 6-bromo-2-chloromethyl-3-methylbenzo[b]thiophene. A sample crystallised from petrol (b.p. 40°-60°) had m.p. 92°-93°.

Workup

  1. washwashed with water, sodium bicarbonate solution
  2. dry with materialdried (Na2SO4)
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-711bbcada83f44a0a9644dce6063f9d8
Source dataset
uspto-grants-1986_05
Patent number
US04590200

Reaction notes

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