Water → Benzo(B)Thiophene

HRID 1700420Notes

Reaction equation

HRID 1700420 reaction equation
COC1C=CC([C:9]2[S:13][C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[CH:10]=2)=CC=1.COC1C=C(C=C(OC)C=1OC)C(Cl)=O.[Al+3].[Cl-].[Cl-].[Cl-].O>C(Cl)Cl.CCOC(C)=O>[S:13]1[CH:9]=[CH:10][C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]1=2

Participants

7

Reactant 4

HCID 962WaterHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 41373912-(4-Methoxyphenyl)benzothiopheneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 7221Benzo(B)ThiopheneYield 81.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a well-stirred solution of 2-(4′-methoxyphenyl)benzo[b]thiophene (0.081 g, 0.32 mmol) and 3,4,5-trimethoxybenzoyl chloride (0.148 g, 0.64 mmol) in CH2Cl2 (15 mL) was added AlCl3 (0.144 g, 1.08 mmol) portion-wise over a 5 minute period. After 3 h 20 min, 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, 90:10 hexane/EtOAc then with 80:20 hexane/EtOAc) afforded desired benzo[b]thiophene (0.035 g, 26%) as white solid. 1H-NMR-(CDCl3, 360 MHz) δ7.87 (m, 1H, ArH), 7.78 (m, 1H, ArH), 7.37 (m, 4H, ArH), 7.07 (s, 2H, ArH), 6.76 (d, J=6.7, 2H, ArH), 3.84 (s, 3H, —OCH3), 3.75 (s, 3H, —OCH3), 3.73 (S, 6H, —OCH3).

Workup

  1. washThe organic layers were separately washed with brine
  2. dry with materialdried over MgSO4
  3. customPurification by flash chromatography (silica gel, 90:10 hexane/EtOAc

Sources & evidence

ORD record
ord-04fb1fc13b0e47c3bc64bf6d7d37ae12
Source dataset
uspto-grants-2002_02
Patent number
US06350777B2

Reaction notes

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