Boron tribromide → 3-Nitro-4-phenylphenol

HRID 1518634Notes

Reaction equation

HRID 1518634 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:5]([N+:15]([O-:17])=[O:16])[CH:4]=1.B(Br)(Br)Br>ClCCl>[N+:15]([C:5]1[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][C:6]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 114019374-Methoxy-2-nitro-biphenyl

Product 1

HCID 121698073-Nitro-4-phenylphenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Methoxy-2-nitro-1-phenylbenzene (1.86 g, 8.31 mmol) was dissolved in dichloromethane (40 mL) and thereto was added, under ice-water cooling, a solution of boron tribromide (2 mL) in dichloromethane (10 mL) After stirring at room temperature for 18 hours, the reaction mixture was poured onto ice to stop the reaction and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 3-nitro-4-phenylphenol as a crude material.

Workup

  1. additionwas added, under ice-water cooling
  2. additionthe reaction mixture was poured onto ice
  3. customthe reaction
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f1b6d565811542948de0849710533e13
Source dataset
uspto-grants-2015_07
Patent number
US09072734B2

Reaction notes

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