Water → 2-Cyano-3-(3-chloro-4, 5-dihydroxyphenyl) propenanilide

HRID 439555Notes

Reaction equation

HRID 439555 reaction equation
[C:1]([C:3](=[CH:13][C:14]1[CH:19]=[C:18]([O:20]C)[C:17]([OH:22])=[C:16]([Cl:23])[CH:15]=1)[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5])#[N:2].B(Br)(Br)Br.O>C(Cl)Cl>[C:1]([C:3](=[CH:13][C:14]1[CH:19]=[C:18]([OH:20])[C:17]([OH:22])=[C:16]([Cl:23])[CH:15]=1)[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:5])#[N:2]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 541812382-Cyano-3-(3-chloro-4-hydroxy-5-methoxyphenyl) propenanilide

Product 1

HCID 542762882-Cyano-3-(3-chloro-4, 5-dihydroxyphenyl) propenanilideYield 80.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-cyano-3-(3-chloro-4-hydroxy-5-methoxyphenyl) propenanilide (340 mg, 1.03 mmol) in methylene chloride (20 ml) chilled at -70° C. was dropwise added 1M solution of boron tribromide in methylene chloride (2.50 ml, 2.5 mmol). The reaction mixture was gradually allowed to warm to room temperature and poured into water. The product was extracted with ethyl acetate, dried over MgSO4 and concentrated. The resulting solid was suspended in diethyl ether, refluxed for 10 minutes and the resultant solid was filtered to give the objective 2-cyano-3-(3-chloro-4, 5-dihydroxyphenyl) propenanilide (260 mg, 80% in yield).

Workup

  1. extractionThe product was extracted with ethyl acetate
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. temperaturerefluxed for 10 minutes
  5. filtrationthe resultant solid was filtered

Sources & evidence

ORD record
ord-340296bba2ae42fa9afe4b5852d2e0bb
Source dataset
uspto-grants-1996_05
Patent number
US05514711

Reaction notes

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