Boron tribromide → 2-Cyano-5-hydroxybenzamide

HRID 1379247Notes

Reaction equation

HRID 1379247 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:9]([O:12]C)=[CH:8][C:4]=1[C:5]([NH2:7])=[O:6])#[N:2].B(Br)(Br)Br>C(Cl)Cl.O>[C:1]([C:3]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:4]=1[C:5]([NH2:7])=[O:6])#[N:2]

Participants

5

Reactant 2

HCID 25134Boron tribromide2×HCID 53933311HCID 53933311, compound

Product 1

HCID 450846212-Cyano-5-hydroxybenzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

A mixture of 2-cyano-5-methoxybenzamide (5.2 g, 0.027 mol) in methylene chloride is cooled to 0° C., treated dropwise with boron tribromide (54 mL of a 1M solution in methylene chloride), stirred at 0° C. for 30 minutes, stirred at room temperature for 1 hour, refluxed for 4 hours, cooled to 0° C., treated with additional boron tribromide (54 mL of a 1M solution in methylene chloride), refluxed for 17 hours, cooled to room temperature and diluted with water. The aqueous mixture is filtered to obtain a solid which is washed sequentially with water and ether and dried to give the title product as a beige solid, mp 268°-270° C.

Workup

  1. stirringstirred at room temperature for 1 hour
  2. temperaturerefluxed for 4 hours
  3. temperaturecooled to 0° C.
  4. temperaturerefluxed for 17 hours
  5. temperaturecooled to room temperature
  6. filtrationThe aqueous mixture is filtered
  7. customto obtain a solid which
  8. washis washed sequentially with water and ether
  9. customdried

Sources & evidence

ORD record
ord-ccd116c3f27643d0ac958e9c6bacdcf8
Source dataset
uspto-grants-1997_09
Patent number
US05670641

Reaction notes

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