Dichloromethane → (2-Benzyl-6-methoxy-benzo[b]thiophen-3-yl)-(4-methoxy-phenyl)-methanone

HRID 1873123Notes

Reaction equation

HRID 1873123 reaction equation
[Sn](Cl)(Cl)(Cl)Cl.[CH2:6]([C:13]1[S:17][C:16]2[CH:18]=[C:19]([O:22][CH3:23])[CH:20]=[CH:21][C:15]=2[CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:24](Cl)(=[O:33])[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1.ClCCl>O>[CH2:6]([C:13]1[S:17][C:16]2[CH:18]=[C:19]([O:22][CH3:23])[CH:20]=[CH:21][C:15]=2[C:14]=1[C:24]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)=[O:33])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7477p-Anisoyl chlorideHCID 24287Tin tetrachlorideHCID 186877862-Benzyl-6-methoxy-benzo[b]thiophene

Product 1

HCID 15481275(2-Benzyl-6-methoxy-benzo[b]thiophen-3-yl)-(4-methoxy-phenyl)-methanoneYield 58.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Tin tetrachloride (2.0 mL, 17.09 mmol) was added dropwise over a 10 minute period to a stirred, -78° C. solution of 2-benzyl-6-methoxy-benzo[b]thiophene (2.71 g, 10.65 mmol), anisoyl chloride (1.93 g, 11.29 mmol) and dichloromethane (41 mL) under a dry nitrogen atmosphere. After 1 hours at -78° C., the reaction mixture was slowly warmed to room temperature and stirred for 16 h period. The reaction mixture was added to water and extracted with ether. The ether phase was washed with brine and silica gel was added to it. The solvent was removed and the adsorbate was flash chromatographed (eluent: 9:1 petroleum ether: ethyl acetate) to provide the title compound as a white solid (2.42 g, 58%): mp 110-112° C.: NMR (CDCl3); δ 7.84 (d, J=9 Hz, 2H), 7.31-7.18 (m, 7H), 7.92 (d, J=9 Hz, 2H), 6.97 (dd, J=9, 2 Hz, 1H), 4.17 (s, 2H), 3.88 (s, 3H), 3.883 (s, 3H); MS (FAB+): 389 (80%, M+H); Anal. Calc. for C24H20O3S: C, 74.20, H, 5.19, N, 0.00. Found: C, 74.94, H, 5.10, N, 0.03.

Workup

  1. extractionextracted with ether
  2. washThe ether phase was washed with brine and silica gel
  3. additionwas added to it
  4. customThe solvent was removed
  5. customchromatographed (eluent: 9:1 petroleum ether: ethyl acetate)

Sources & evidence

ORD record
ord-575c11a0c03446e089de3f29cf9e07d0
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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