Dichloromethane → N-(3-chlorophenyl)-2-cyano-3-(3-fluoro-4, 5-dihydroxyphenyl) propenamide

HRID 439560Notes

Reaction equation

HRID 439560 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:24])[C:10]([C:22]#[N:23])=[CH:11][C:12]2[CH:17]=[C:16]([O:18]C)[C:15]([OH:20])=[C:14]([F:21])[CH:13]=2)[CH:5]=[CH:6][CH:7]=1.B(Br)(Br)Br.C(Cl)Cl>>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:24])[C:10]([C:22]#[N:23])=[CH:11][C:12]2[CH:17]=[C:16]([OH:18])[C:15]([OH:20])=[C:14]([F:21])[CH:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 54180841N-(3-chlorophenyl)-2-cyano-3-(3-fluoro-4-hydroxy-5-methoxyphenyl) propenamide

Product 1

HCID 53807593N-(3-chlorophenyl)-2-cyano-3-(3-fluoro-4, 5-dihydroxyphenyl) propenamideYield 35.4%

Procedure

Demethylation was effected in the same as in Example 2 with N-(3-chlorophenyl)-2-cyano-3-(3-fluoro-4-hydroxy-5-methoxyphenyl) propenamide (470 mg, 1.36 mmol) and 1M solution of boron tribromide in methylene chloride (3.50 ml, 34.50 mmol). The resulting solid was recrystallized from ethanol-water to give the objective N-(3-chlorophenyl)-2-cyano-3-(3-fluoro-4, 5-dihydroxyphenyl) propenamide (160 mg, 35% in yield) as yellow powder.

Workup

  1. customThe resulting solid was recrystallized from ethanol-water

Sources & evidence

ORD record
ord-557406200f464b6c932d0c9a23b9f7c3
Source dataset
uspto-grants-1996_05
Patent number
US05514711

Reaction notes

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