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

HRID 439558Notes

Reaction equation

HRID 439558 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]([Br:21])[CH:13]=2)[CH:5]=[CH:6][CH:7]=1.B(Br)(Br)Br.C(Cl)Cl>C(O)C>[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]([Br:21])[CH:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 53730904N-(3-chlorophenyl)-2-cyano-3-(3-bromo-4-hydroxy-5-methoxyphenyl) propenamide

Product 1

HCID 54561038N-(3-chlorophenyl)-2-cyano-3-(3-bromo-4, 5-dihydroxyphenyl) propenamideYield 27%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Demethylation was effected in the same manner as in Example 2 with N-(3-chlorophenyl)-2-cyano-3-(3-bromo-4-hydroxy-5-methoxyphenyl) propenamide (1.38 g, 3.39 mmol) and 1M solution of boron tribromide in methylene chloride (8.5 ml, 8.5 mmol). The resultant solid was mixed with ethanol, refluxed for 10 minutes, allowed to cool to room temperature and filtered to give the objective N-(3-chlorophenyl)-2-cyano-3-(3-bromo-4, 5-dihydroxyphenyl) propenamide (360 mg, 27% in yield).

Workup

  1. temperaturerefluxed for 10 minutes
  2. filtrationfiltered

Sources & evidence

ORD record
ord-7e99a5b810e9439bb6caec91aea7b668
Source dataset
uspto-grants-1996_05
Patent number
US05514711

Reaction notes

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