Boron tribromide → 3-Hydroxy-5-nitrobenzotrifluoride

HRID 871436Notes

Reaction equation

HRID 871436 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[C:5]([N+:13]([O-:15])=[O:14])[CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[N+:13]([C:5]1[CH:4]=[C:3]([OH:2])[CH:8]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:6]=1)([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 5205973-Methoxy-5-nitrobenzotrifluoride

Product 1

HCID 27562513-Hydroxy-5-nitrobenzotrifluorideYield 37.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1-methoxy-3-nitro-5-(trifluoromethyl)benzene (2.21 g, 10.0 mmol) in DCM at 0° C. was added BBr3 (10 equivalents) dropwise over 5 minutes. The solution was allowed to warm to r.t overnight at which point it was quenched with sat. aqueous NaHCO3 and extracted with EtOAc. The organic layer was washed with H2O and brine, dried over MgSO4, filtered, and concentrated in vacuo to give 3-nitro-5-(trifluoromethyl)phenol (778 mg, 3.76 mmol, 37%), 1H NMR (300 MHz, DMSO-d6) δ 11.22 (s, 1H), 7.90 (s, 1H), 7.81 (s, 1H), 7.51 (s, 1H); LC-MS (ESI) m/z 208 (M+H)+.

Workup

  1. temperatureto warm
  2. customwas quenched with sat. aqueous NaHCO3
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with H2O and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-38490fd404ad4778b34fb7c0b885f343
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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