Dimethyl Sulfide → 5-Chloro-1-benzothiophene-2-carbaldehyde

HRID 27929Notes

Reaction equation

HRID 27929 reaction equation
ClN1C(=O)CCC1=O.CSC.[Cl:12][C:13]1[CH:14]=[CH:15][C:16]2[S:20][C:19]([CH2:21][OH:22])=[CH:18][C:17]=2[CH:23]=1.C(N(CC)CC)C>CCOCC.C1(C)C=CC=CC=1>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]2[S:20][C:19]([CH:21]=[O:22])=[CH:18][C:17]=2[CH:23]=1

Participants

7

Reactant 4

HCID 1068Dimethyl SulfideHCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 23340421(5-Chloro-1-benzothiophen-2-yl)methanol

Product 1

HCID 184670505-Chloro-1-benzothiophene-2-carbaldehyde

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a mixture of N-chlorosuccinimide (13.1 mmol) and 50 ml toluene, at 0°, is slowly added dimethylsulfide (18.1 mmol). The mixture is stirred briefly, cooled to -25° and 5-chlorobenzothiophene-2-methanol (10. 1 mmol) added followed by stirring for 2 hours. Triethylamine (13.1 mmol) is added and the mixture allowed to warm to RT. The mixture is taken up in ether, washed with 10% HCl, water and brine, dried over sodium sulfate and solvent removed to give 5-chlorobenzothiophene-2-carboxaldehyde.

Workup

  1. customat 0°
  2. temperaturecooled to -25°
  3. stirringby stirring for 2 hours
  4. washwashed with 10% HCl, water and brine
  5. dry with materialdried over sodium sulfate and solvent
  6. customremoved

Sources & evidence

ORD record
ord-5a47ab609269458dba42d18c029a9c54
Source dataset
uspto-grants-1980_09
Patent number
US04224330

Reaction notes

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