Boron tribromide → N,N-Diethyl-2'-hydroxy[1,1'-biphenyl]-4-carboxamide

HRID 895620Notes

Reaction equation

HRID 895620 reaction equation
[CH2:1]([N:3]([CH2:20][CH3:21])[C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18]C)=[CH:8][CH:7]=1)=[O:5])[CH3:2].B(Br)(Br)Br>ClCCl>[CH2:20]([N:3]([CH2:1][CH3:2])[C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[OH:18])=[CH:8][CH:7]=1)=[O:5])[CH3:21]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 223807362-(4-Diethylcarbamoylphenyl)anisole

Product 1

HCID 22380635N,N-Diethyl-2'-hydroxy[1,1'-biphenyl]-4-carboxamideYield 97.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(4-Diethylcarbamoylphenyl)anisole (250 mg) was dissolved in dichloromethane (10 ml), added with boron tribromide (0.42 ml) and stirred at room temperature for 3 hours. After the reaction mixture was slowly poured into ice (20 g) with ice cooling to quench the reaction and the layers were separated, the aqueous layer was extracted with dichloromethane (10 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=2:1→1:1) to obtain 231 mg of the title compound. Yield: 97%.

Workup

  1. customto quench
  2. customthe reaction
  3. customthe layers were separated
  4. extractionthe aqueous layer was extracted with dichloromethane (10 ml)
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=2:1→1:1)

Sources & evidence

ORD record
ord-06ac1ef86a9d444aafff9ac676a6c4ed
Source dataset
uspto-grants-2005_07
Patent number
US06916822B2

Reaction notes

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