Water → 7-Methyl-1-benzothiophene
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- temperatureat reflux for 18 h
- extractionthe organic material was extracted with CH2Cl2 (2×50 mL)
- dry with materialThe organic solution was dried (MgSO4)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-88550aaae67648ecb73cc15c04d7fd70
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08039458B2
Reaction notes
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