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

HRID 1871313Notes

Reaction equation

HRID 1871313 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 dichioromethyl 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 (2N) 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 C16H12Os : 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-f05b4a57de494ba3abf83179f75500e6
Source dataset
uspto-grants-2000_08
Patent number
US06103708

Reaction notes

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