Thionyl Chloride → 4-(Chloromethyl)-1-(cyclohexylmethyl)-2-(trifluoromethyl)benzene

HRID 515697Notes

Reaction equation

[CH:1]1([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14]O)=[CH:10][C:9]=2[C:16]([F:19])([F:18])[F:17])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:22])=O>C1(C)C=CC=CC=1>[Cl:22][CH2:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[C:9]([C:16]([F:19])([F:18])[F:17])[CH:10]=1

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of (4-(cyclohexylmethyl)-3-(trifluoromethyl)phenyl)methanol (0.060 g, 0.220 mmol) in toluene (2 mL) was added thionyl chloride (1.32 mmol). The reaction was heated to 75° C. for 3 h and quenched with water at 0° C. The mixture was extracted with hexanes (twice). The combined organics were washed with saturated NaHCO3(aq), dried over MgSO4, and concentrated to give the title compound as an oil (0.220 mmol). 1H NMR (400 MHz, CDCl3) δ ppm 0.91-1.06 (m, 2H), 1.12-1.23 (m, 3H), 1.61-1.74 (m, 6H), 2.66 (d, J=6.95 Hz, 2H), 4.59 (s, 2H), 7.30 (d, J=7.96 Hz, 1H), 7.47 (d, J=7.96 Hz, 1H), 7.63 (s, 1H).

Workup

customquenched with water at 0° C
extractionThe mixture was extracted with hexanes (twice)
washThe combined organics were washed with saturated NaHCO3(aq)
dry with materialdried over MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-897cc3b67f094b319fa856663e0df3f8
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09108969B2

Reaction notes

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