Water → 7-Methyl-1-benzothiophene

HRID 1664174Notes

Reaction equation

HRID 1664174 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 (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-88550aaae67648ecb73cc15c04d7fd70
Source dataset
uspto-grants-2011_10
Patent number
US08039458B2

Reaction notes

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