Thionyl Chloride → 8-Chloro-3-(chloromethyl)-2-(2-trifluoromethylphenyl)quinoline

HRID 2074498Notes

Reaction equation

HRID 2074498 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([F:21])([F:20])[F:19])[C:8]([CH2:22]O)=[CH:7]2.O=S(Cl)[Cl:26]>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([F:21])([F:20])[F:19])[C:8]([CH2:22][Cl:26])=[CH:7]2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 57556184(8-Chloro-2-(2-trifluoromethylphenyl)quinolin-3-yl)methanol

Product 1

HCID 575561498-Chloro-3-(chloromethyl)-2-(2-trifluoromethylphenyl)quinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared according to Procedure C using (8-chloro-2-(2-trifluoromethylphenyl)quinolin-3-yl)methanol (1.10 g, 3.26 mmol) and SOCl2 (1.19 mL, 16.3 mmol, 5 eq) in dichloromethane (5 mL). 8-chloro-3-(chloromethyl)-2-(2-trifluoromethylphenyl)quinoline was obtained as a yellow syrup. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.75 (1 H, s), 8.10 (1 H, d, J=8.2 Hz), 8.02 (1 H, d, J=6.3 Hz), 7.95 (1H, d, J=7.4 Hz), 7.72-7.87 (2 H, m), 7.58-7.71 (2 H, m), 4.71 (2 H, dd, J=82.2, 12.1 Hz) Mass Spectrum (ESI) m/e=356.0 and 358.0 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-124c38d558b847d9b5b2034986c166ab
Source dataset
uspto-grants-2011_04
Patent number
US07919498B2

Reaction notes

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