Dichloromethane → HCID 67595118, compound

HRID 611735Notes

Reaction equation

HRID 611735 reaction equation
[Sn](Cl)(Cl)(Cl)Cl.[CH3:6][CH:7]=[CH:8][C:9]1[S:13][C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=2[CH:10]=1.[C:18](Cl)(=[O:27])[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1.ClCCl>O>[CH3:6][CH:7]=[CH:8][C:9]1[S:13][C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=2[C:10]=1[C:18]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)=[O:27]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7477p-Anisoyl chlorideHCID 24287Tin tetrachlorideHCID 67593962HCID 67593962, compound

Product 1

HCID 67595118HCID 67595118, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Tin tetrachloride (2.83 mL, 24.12 mmol) was added dropwise over a 10 minute period to a stirred solution of 2-all-3-yl-benzo[b]thiophene (3.51 g, 20.1 mmol), anisoyl chloride (3.61 g, 21.1 mmol) and dichloromethane (70 mL) under a dry nitrogen atmosphere. After 5 h., the mixture was warmed up and stirred at 0° C. for 1 h. The reaction mixture was added to water and extracted with ethyl ether. The ethyl ether extract was washed with sat. aq. sodium bicarbonate and brine. Silica gel (100 mL) was added. Solvents were removed and the silica adsorbate was flash chromatographed (eluent 92:8 petroleum ether:ethyl acetate) to provide the title compound as an oil (4.42 g, 71 %): NMR (CDCl3); δ 7.88-7.76 (multiplet with overlapping doublet at 7.84, J=9 Hz, 3H), 7.50-7.44 (m, 1H), 7.34-7.24 (m, 2H), 6.94 (d, J=9 Hz, 2H), 6.00-5.85 (m, 1H), 5.20-5.13 (m, 2H), 3.90 (s, 3H), 3.62 (d, J=6 Hz, 2H); MS (EI): [M+] 308 (50%); Anal. Calc. for C19H16O2S: C, 74.00, H, 5.23, N, 0.00. Found: C, 73.16, H, 5.13, N, 0.09.

Workup

  1. temperaturethe mixture was warmed up
  2. extractionextracted with ethyl ether
  3. extractionThe ethyl ether extract
  4. washwas washed with sat. aq. sodium bicarbonate and brine
  5. additionSilica gel (100 mL) was added
  6. customSolvents were removed
  7. customchromatographed (eluent 92:8 petroleum ether:ethyl acetate)

Sources & evidence

ORD record
ord-b43721dc624844a68d827e67646a011a
Source dataset
uspto-grants-1999_12
Patent number
US06001867

Reaction notes

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