Hydrochloric Acid → HCID 22267251, compound

HRID 488871Notes

Reaction equation

HRID 488871 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[C:7]([CH2:13][C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=3[C:24]([F:27])([F:26])[F:25])=[O:15])[C:8](=[O:12])[O:9]2)=[CH:4][C:3]=1[O:34]C.B(Br)(Br)Br.C(Cl)Cl.Cl>C(Cl)Cl>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[C:7]([CH2:13][C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=3[C:24]([F:26])([F:25])[F:27])=[O:15])[C:8](=[O:12])[O:9]2)=[CH:4][C:3]=1[OH:34]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 22267285HCID 22267285, compoundHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 22267251HCID 22267251, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(7-chloro-6-methoxy-2-oxo-4-phenyl-2H-chromen-3-yl)-N-[4-chloro-2-(trifluoromethyl)phenyl]acetamide (Example 178) (3.20 g) in methylene chloride (10 ml) was combined with a 1 M solution of boron tribromide/methylene chloride (31.6 ml, 13.6 mmol), and stirred at room temperature for 3 days. The reaction solution was poured into an ice water, to which concentrated hydrochloric acid was then added. The precipitate was filtered and washed with isopropanol followed by ether to obtain the title compound as a colorless crystal (2.05 g, 64%). An aliquot was recrystallized from THF-isopropyl ether to measure a melting point. Melting point: 246-247° C.

Workup

  1. additionwas then added
  2. filtrationThe precipitate was filtered
  3. washwashed with isopropanol

Sources & evidence

ORD record
ord-5aea697fbe5c444188efe0117a2a47be
Source dataset
uspto-grants-2005_12
Patent number
US06974806B2

Reaction notes

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