Water → Benzo(B)Thiophene

HRID 1700421Notes

Reaction equation

HRID 1700421 reaction equation
C(OC1C=CC([C:10]2[S:14][C:13]3[CH:15]=[C:16](OCC)[CH:17]=[CH:18][C:12]=3[CH:11]=2)=CC=1)C.COC1C=C(C=C(OC)C=1OC)C(Cl)=O.[Al+3].[Cl-].[Cl-].[Cl-].O>C(Cl)Cl.CCOC(C)=O>[S:14]1[CH:10]=[CH:11][C:12]2[CH:18]=[CH:17][CH:16]=[CH:15][C:13]1=2

Participants

7

Reactant 4

HCID 962WaterHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 6451240Aluminum(III) ChlorideHCID 18318587HCID 18318587, compound

Product 1

HCID 7221Benzo(B)ThiopheneYield 69%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a well-stirred solution of 2-(4′-ethoxyphenyl)-6-ethoxybenzo[b]thiophene (0.095 g, 0.32 mmol) and 3,4,5-trimethoxybenzoyl chloride (0.159 g, 0.69 mmol) in CH2Cl2 (15 mL) was added AlCl3 (0.139 g, 1.04 mmol) portion-wise over a 5 minute period. After 30 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, 80:20 hexane/EtOAc) afforded benzo[b]thiophene (0.110 g, 0.2 mmol, 69%) as an off-white solid. 1H-NMR (CDCl3, 360 Mhz) δ7.65 (d, J=8.9 Hz, 1H, ArH), 7.32 (d, J=2.3 Hz, 1H, ArH), 7.29 (d, J=8.8 Hz, 2H, ArH), 7.06 (s, 2H, ArH), 7.00 (dd, J=8.9, 2.4 Hz, 1H, ArH), 6.73 (d, J=8.7 Hz, 2H, ArH), 4.12 (q, J=7.0 Hz, 2H, —CH2), 3.97 (q, J=6.9 Hz, 2H, —CH2), 3.83 (s, 3H, —OCH3), 3.73 (S, 6H, —OCH3), 1.47 (t, J=6.9 Hz, 3H, —CH3), 1.37 (t, J=7.0 Hz, 3H, —CH3).

Workup

  1. washThe organic layers were separately washed with brine
  2. dry with materialdried over MgSO4
  3. customPurification by flash chromatography (silica gel, 80:20 hexane/EtOAc)

Sources & evidence

ORD record
ord-a7a5cb752be6484e9615383b55e8c668
Source dataset
uspto-grants-2002_02
Patent number
US06350777B2

Reaction notes

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