Boron tribromide → HCID 54212167, compound

HRID 439556Notes

Reaction equation

HRID 439556 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]([Cl: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]([Cl:21])[CH:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 53928460HCID 53928460, compound

Product 1

HCID 54212167HCID 54212167, compoundYield 44.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

Demethylation was effected in the same manner as in Example 2 by using N-(3-chlorophenyl)-2-cyano-3-(3-chloro-4-hydroxy-5-methoxyphenyl) propenamide (587 mg, 1.62 mmol) and 1M solution of boron tribromide in methylene chloride. The resulting solid was suspended in ethanol, refluxed for 10 minutes, allowed to cool to room temperature and filtered to give the objective N-(3-chlorophenyl)-2-cyano-3-(3-chloro-4, 5-dihydroxyphenyl)propenamide (250 mg, 44% in yield).

Workup

  1. temperaturerefluxed for 10 minutes
  2. filtrationfiltered

Sources & evidence

ORD record
ord-b3c3cfb9b67147ad8a0cfc39dc5d2af2
Source dataset
uspto-grants-1996_05
Patent number
US05514711

Reaction notes

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