Thionyl Chloride → 2-(Chloromethyl)-5-nitro-1-benzothiophene

HRID 467106Notes

Reaction equation

HRID 467106 reaction equation
S(Cl)([Cl:3])=O.[N+:5]([C:8]1[CH:18]=[CH:17][C:11]2[S:12][C:13]([CH2:15]O)=[CH:14][C:10]=2[CH:9]=1)([O-:7])=[O:6]>N1C=CC=CC=1.ClCCl>[Cl:3][CH2:15][C:13]1[S:12][C:11]2[CH:17]=[CH:18][C:8]([N+:5]([O-:7])=[O:6])=[CH:9][C:10]=2[CH:14]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 12182118(5-nitrobenzo[b]thiophen-2-yl)methanol

Product 1

HCID 151337582-(Chloromethyl)-5-nitro-1-benzothiophene

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (1.0 ml) was added dropwise to a stirred mixture of 5-nitrobenzo[b]thiophene-2-methanol (1.0 g) and pyridine (2 drops) in dichloromethane (10 ml). The solution was stirred at room temperature for 4 hours and then washed with water followed by aqueous sodium bicarbonate solution, and then dried (Na2SO4). The solvent was evaporated and the residue was chromatographed on silica gel. Elution with dichloromethane gave a solid which was crystallised from ethyl acetate to give the title compound (0.73 g), m.p. 110°-112°, used directly in the next stage.

Workup

  1. washwashed with water
  2. dry with materialdried (Na2SO4)
  3. customThe solvent was evaporated
  4. customthe residue was chromatographed on silica gel
  5. washElution with dichloromethane
  6. customgave a solid which
  7. customwas crystallised from ethyl acetate

Sources & evidence

ORD record
ord-746a2ee723d049ccbe836fa522a08d8f
Source dataset
uspto-grants-1992_10
Patent number
US05158964

Reaction notes

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