Thionyl Chloride → 5-(Chloromethyl)-2-cyclohexylbenzonitrile

HRID 2274059

Reaction equation

HRID 2274059 reaction equation
[CH:1]1([C:7]2[CH:14]=[CH:13][C:12]([CH2:15]O)=[CH:11][C:8]=2[C:9]#[N:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:19])=O>>[Cl:19][CH2:15][C:12]1[CH:13]=[CH:14][C:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[C:8]([CH:11]=1)[C:9]#[N:10]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 580205132-Cyclohexyl-5-(hydroxymethyl)benzonitrile

Product 1

HCID 672113535-(Chloromethyl)-2-cyclohexylbenzonitrileYield 89.4%

Conditions

Temperature
50 °C

Procedure

To 2-cyclohexyl-5-(hydroxymethyl)benzonitrile (190.5 mg, 0.885 mmol) was added thionyl chloride (5.0 mL, 68.1 mmol). The mixture was heated at 50° C. for 2 h and then room temperature overnight. The mixture was poured into an ice and stirred for 5 min. The mixture was extracted with dichloromethane. The organic layer was washed with saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure to provide the title compound as a white solid (184.9 mg). LCMS m/z=234.1 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 1.23-1.31 (m, 1H), 1.40-1.52 (m, 4H), 1.76-1.82 (m, 1H), 1.83-1.92 (m, 4H), 2.93-3.03 (m, 1H), 4.55 (s, 2H), 7.37 (d, J=8.08 Hz, 1H), 7.55 (dd, J=8.02, 1.83 Hz, 1H), 7.62 (d, J=1.64 Hz, 1H).

Workup

  1. customroom temperature overnight
  2. extractionThe mixture was extracted with dichloromethane
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7e7e5557eb99406693955bf02b719d62
Source dataset
uspto-grants-2015_09
Patent number
US09126932B2

Linked notes

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