Water → 7-Methyl-1-benzothiophene

HRID 1726606Notes

Reaction equation

HRID 1726606 reaction equation
C(O[CH:4](OCC)[CH2:5][S:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH3:13])C.O>ClC1C=CC=CC=1>[CH3:13][C:8]1[C:7]2[S:6][CH:5]=[CH:4][C:12]=2[CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 962WaterHCID 10610097(2,2-Diethoxyethyl)(o-tolyl)sulfane

Product 1

HCID 64285417-Methyl-1-benzothiopheneYield 94%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

To a solution of intermediate 136, (2,2-diethoxyethyl)(o-tolyl)sulfane (0.58 g, 2.41 mmol) in chlorobenzene (20 mL) was added polyphosphoric acid. The reaction mixture was stirred at reflux for 18 h. Water (100 mL) was then added and the organic material was extracted with CH2Cl2 (2×50 mL). The organic solution was dried (MgSO4) and concentrated in vacuo to afford 335 mg (94% yield) of the title compound: 1H NMR (400 MHz, CDCl3) δ: 7.68 (1H, d, J=7.8 Hz), 7.43 (1H, d, J=5.4 Hz), 7.36 (1H, d, J=5.4 Hz), 7.30 (1H, dd, J=7.8, 7.1 Hz), 7.14 (1H, d, J=7.1 Hz), 2.58 (3H, s); LCMS (M+H)+ m/z 148.

Workup

  1. temperatureat reflux for 18 h
  2. extractionthe organic material was extracted with CH2Cl2 (2×50 mL)
  3. dry with materialThe organic solution was dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f6b82ae6128d4791ba3fd9dec41ba60b
Source dataset
uspto-grants-2009_02
Patent number
US07491819B1

Reaction notes

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