Thionyl Chloride → HCID 57707798, compound

HRID 216862Notes

Reaction equation

HRID 216862 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[F:22])[C:12]([CH2:23]O)=[CH:11]2>C(Cl)Cl>[Cl:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[F:22])[C:12]([CH2:23][Cl:3])=[CH:11]2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 57707816HCID 57707816, compound

Product 1

HCID 57707798HCID 57707798, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (0.850 mL, 11.6 mmol) was added to a stirring solution of (8-chloro-2-(2-fluorophenyl)quinolin-3-yl)methanol (0.670 g, 2.33 mmol) in CH2Cl2. The reaction mixture was stirred at room temperature. After 2.5 h, the crude product was purified by column chromatography on a 40 g Redi-Sep™ column using 0% to 100% gradient of CH2Cl2-MeOH-NH4OH (89:9:1) in CH2Cl2 to give 8-chloro-3-(chloromethyl)-2-(2-fluorophenyl)quinoline: LC-MS (ESI) m/z 306.0 [M+H]+.

Workup

  1. customthe crude product was purified by column chromatography on a 40 g Redi-Sep™ column

Sources & evidence

ORD record
ord-e89746d57c1246bfa1e19b1ba68451fe
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Reaction notes

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