Hydrochloric Acid → 2-Benzyl-benzo[b]thiophene-3-carboxaldehyde

HRID 1280902Notes

Reaction equation

HRID 1280902 reaction equation
[Sn](Cl)(Cl)(Cl)Cl.[CH2:6]([C:13]1[S:17][C:16]2[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=2[CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:22][O:23]C(Cl)Cl.Cl>ClCCl>[CH2:6]([C:13]1[S:17][C:16]2[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=2[C:14]=1[CH:22]=[O:23])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 21004Methane, dichloromethoxy-HCID 24287Tin tetrachlorideHCID 127581572-Benzyl-1-benzothiophene

Product 1

HCID 234456472-Benzyl-benzo[b]thiophene-3-carboxaldehydeYield 85.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tin chloride (14.0 mL, 119.6 mmol) was added dropwise into a cold (−20° C.) solution of 2-benzyl-benzo[b]thiophene (13.4 g, 59.8 mmol) in dichloromethane (150.0 mL). After 1 h, to the reaction was added dropwise dichloromethyl methyl ether (119.6 mmol). The mixture was allowed to gradually come to 0° C., and then stirred for 20 hours. The mixture was carefully poured into HCl (2 N) and ice, and extracted with ethyl ether. The ethereal extracts were dried (MgSO4) and concentrated to give 12.9 g (85%) of the title compound after crystallization from ethyl ether/hexanes, yellow solid mp 86-88° C.; mass spectrum m/z 252 (M+). Anal. Calcd. for C16H12O5: C 76.16; H, 4.79. Found: C, 75.77; H, 4.85

Workup

  1. customto gradually come to 0° C.
  2. extractionextracted with ethyl ether
  3. dry with materialThe ethereal extracts were dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-037fd4997fe347d3adf3c1d947d0c485
Source dataset
uspto-grants-2002_09
Patent number
US06451845B1

Reaction notes

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