Chloroform → HCID 86630638, compound

HRID 216851Notes

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]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[C:19]([F:22])([F:21])[F:20])[C:8]([CH2:23]O)=[CH:7]2.C(Cl)(Cl)[Cl:26].S(Cl)(Cl)=O>>[ClH:1].[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]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[C:19]([F:22])([F:21])[F:20])[C:8]([CH2:23][Cl:26])=[CH:7]2

Participants

Reactant 3

HCID 6212Chloroform

HCID 24386Thionyl Chloride

HCID 57707799HCID 57707799, compound

Product 1

HCID 86630638HCID 86630638, compound

Procedure

A solution of (8-chloro-2-(5-fluoro-2-(trifluoromethyl)phenyl)quinolin-3-yl)-methanol (0.3016 g, 0.8479 mmol) in chloroform (2.826 mL, 0.8479 mmol) was treated with thionyl chloride (0.3085 mL, 4.239 mmol) dropwise, and the reaction mixture was stirred at room temperature. After 3 h, the mixture was concentrated under reduced pressure and co-evaporated three times with CH2Cl2 to give 8-chloro-3-(chloromethyl)-2-(5-fluoro-2-(trifluoromethyl)phenyl)quinoline hydrochloride as a yellow syrup: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.76 (1H, s), 8.11 (1H, dd, J=8.2, 1.2 Hz), 7.99-8.07 (2H, m), 7.60-7.75 (3H, m), 4.63-4.90 (2H, m); LC-MS (ESI) m/z [M+H]+ (Exact Mass of neutral form: 373.005). The yellow syrup was carried on crude without purification for the next step.

Workup

concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record: ord-a4175c61865e4e15a90b100bec0b26d7
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193199B2

Reaction notes

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