Water → 3-(2',6'-Dimethoxybenzoyl)-2-(4'-methoxyphenyl)-6-methoxybenzo[b]thiophene

HRID 1419127Notes

Reaction equation

HRID 1419127 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:11]=3[CH:10]=2)=[CH:5][CH:4]=1.[CH3:20][O:21][C:22]1[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[C:23]=1[C:24](Cl)=[O:25].[Al+3].[Cl-].[Cl-].[Cl-].O>C(Cl)Cl.CCOC(C)=O>[CH3:32][O:31][C:27]1[CH:28]=[CH:29][CH:30]=[C:22]([O:21][CH3:20])[C:23]=1[C:24]([C:10]1[C:11]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:12]=2[S:13][C:9]=1[C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:25]

Participants

7

Reactant 4

HCID 962WaterHCID 748102,6-Dimethoxybenzoyl chlorideHCID 8509416-Methoxy-2-(4-methoxyphenyl)benzo[b]thiopheneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 154112183-(2',6'-Dimethoxybenzoyl)-2-(4'-methoxyphenyl)-6-methoxybenzo[b]thiopheneYield 60%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a well-stirred solution of 2-(4'-methoxyphenyl) - 6-methoxybenzo[b]thiophene (0.500 g, 1.85 mmol) and 2,6-dimethoxybenzoyl chloride (1.11 g, 5.56 mmol) in CH2Cl2 (40 mL) was added AlCl3 (0.986 g, 7.40 mmol) portion-wise over a 15 minute period. After 6 hours, water was added, and the product was isolated initially by extraction with CH2Cl2 and subsequently by extraction with EtOAc. The organic layers were separately washed with brine and then combined and dried over MgSO4. Purification by flash chromatography (silica gel, 60:40 EtOAc/hexane) afforded the title compound (0.484 g, 1.11 mmol, 60%) as an off-white solid. Recrystallization (hexane/ethanol) afforded a highly pure, crystalline sample with mp 146°-152° C.: 1H-NMR (CDCl3, 360 Mhz): δ=8.54 (dd,J=9.1,0.3 Hz, 1H, ArH), 7.25 (d,J=2.1 Hz, 1H, ArH), 7.12 (d,J=8.8 Hz, 2H, ArH), 7.10 (dd,J=9.0,2.5 Hz, 1H, ArH), 6.98 (t,J=8.4 Hz, 1H, ArH), 6.58 (d,J=8.8 Hz, 2H, ArH), 6.20 (d,J=8.4 Hz, 2H, ArH), 3.88 (s,3H, --OCH3), 3.73 (s,3H, --OCH3), 3.60 (s,6H, --OCH3); 13C-NMR (CDCl3, 90 Mhz): δ=190.3, 159.5, 157.5, 157.3, 151.3, 139.3, 132.9, 131.9, 130.8, 130.5, 126.4, 125.7, 120.3 115.0, 112.6, 103.9, 103.6, 55.6, 55.5, 55.3. HRMS (EI) M30 calcd for C25H22O5S 434.1188, found 434.1188.

Workup

  1. washThe organic layers were separately washed with brine
  2. dry with materialdried over MgSO4
  3. customPurification by flash chromatography (silica gel, 60:40 EtOAc/hexane)

Sources & evidence

ORD record
ord-0aaf1cbf6b534c858c413a87da1b1964
Source dataset
uspto-grants-1999_03
Patent number
US05886025

Reaction notes

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