Phosphorus oxychloride → 6-broMo-2-chloro-8-fluoroquinoline

Reaction equation

O=P(Cl)(Cl)[Cl:3].[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[C:15]([F:17])[CH:16]=1)[NH:13][C:12](=O)[CH:11]=[CH:10]2>>[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[C:15]([F:17])[CH:16]=1)[N:13]=[C:12]([Cl:3])[CH:11]=[CH:10]2

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 583494486-Bromo-8-fluoroquinolin-2(1H)-one

Product 1

HCID 583495016-broMo-2-chloro-8-fluoroquinoline

Procedure

Using the POCl3 procedure from INTERMEDIATE 4 Step B, 6-bromo-8-fluoroquinolone was converted to the title compound: LC6: 3.42 min. (M+H) 260.

Sources & evidence

ORD record: ord-a7ab705584334d5781370ac388282475
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436015B2

Reaction notes

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