Thionyl Chloride → 5-(Chloromethyl)-2-(propan-2-yloxy)benzonitrile
Reaction equation
O[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([O:11][CH:12]([CH3:14])[CH3:13])=[C:7]([CH:10]=1)[C:8]#[N:9].S(Cl)([Cl:17])=O>C1(C)C=CC=CC=1>[Cl:17][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([O:11][CH:12]([CH3:14])[CH3:13])=[C:7]([CH:10]=1)[C:8]#[N:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
5-(Hydroxymethyl)-2-isopropoxybenzonitrile (5.96 g, 31.2 mmol) was dissolved in toluene (90 mL) and thionyl chloride (13.65 mL, 187 mmol) was added. The reaction mixture was warmed to 75° C. and stirred for 20 min. The reaction mixture was diluted with hexanes and washed with water and saturated aqueous sodium bicarbonate. The hexane solution was dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound (5.6 g). 1H NMR (400 MHz, CDCl3) δ ppm 1.41 (d, J=6.1 Hz, 6H), 4.52 (s, 2H), 4.66 (septet, J=6.1 Hz, 1H), 6.95 (d, J=8.6 Hz, 1H), 7.51 (dd, J=8.7, 2.4 Hz, 1H), 7.57 (d, J=2.3 Hz, 1H).
Workup
- washwashed with water and saturated aqueous sodium bicarbonate
- dry with materialThe hexane solution was dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-261c42ede52844c38c371c3be626160c
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09126932B2
Reaction notes
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