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

HRID 1700412Notes

Reaction equation

HRID 1700412 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) M+ calcd for C25H22O5S 434.1188, found 434.1188. Anal. Calcd for C25H22O5S: C, 69.11; H, 5.10; S, 7.38. Found: C, 69.19; H, 5.18; S, 7.28.

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-f1401b893d2044078effb0f43a8edc43
Source dataset
uspto-grants-2002_02
Patent number
US06350777B2

Reaction notes

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