Benzoyl chloride, 3,4,5-trimethoxy- → 6-Methoxy-2-methyl-3-(3,4,5-trimethoxybenzoyl)benzo[b]thiophene

HRID 1192020Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[C:9]([CH3:11])[S:8][C:7]=2[CH:12]=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:21]=[C:22]([O:26][CH3:27])[C:23]=1[O:24][CH3:25])[C:18](Cl)=[O:19]>ClCCCl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:18](=[O:19])[C:17]3[CH:16]=[C:15]([O:14][CH3:13])[C:23]([O:24][CH3:25])=[C:22]([O:26][CH3:27])[CH:21]=3)=[C:9]([CH3:11])[S:8][C:7]=2[CH:12]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a mixture of 6-methoxy-2-methylbenzo[b]thiophene (0.024 g; 0.132 mmol) and 3,4,5-trimethoxybenzoyl chloride (0.052 g; 0.225 mmol) in 1,2-dichloroethane (1 ml) SnCl4 (0.023 ml) was added. The resulting mixture was stirred for 1 h at 40° C., quenched with H2O (1 ml), diluted to 15 ml with diethyl ether, washed with 5% NaHCO3 (5 ml), brine (10 ml), dried over anhydrous MgSO4, filtered and filtrate evaporated to dryness under reduced pressure. The residue was purified by flash column chromatography (SiO2; hexane/ethyl acetate 9:1) to give pure title compound (0.020 g; 41%) as a colourless crystals. 1H-NMR (CDCl3) 2.47 (s, 3H); 3.8 (s, 6H); 3.84 (s, 3H); 3.93 (s, 3H); 6.90 (dd, 1H, J=2.4, 8.89 Hz); 7.1 (s, 2H); 7.24 (d, 1H, J=2.4 Hz); 7.42 (d, 1H, J=8.89 Hz).

Workup

additionwas added
customquenched with H2O (1 ml)
additiondiluted to 15 ml with diethyl ether
washwashed with 5% NaHCO3 (5 ml), brine (10 ml)
dry with materialdried over anhydrous MgSO4
filtrationfiltered
customfiltrate evaporated to dryness under reduced pressure
customThe residue was purified by flash column chromatography (SiO2; hexane/ethyl acetate 9:1)

Sources & evidence

ORD record: ord-085f6ebfccaf422db552a078636bc92c
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680135B2

Reaction notes

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