Ethyl Acetate → 3-Hydroxy-5-nitrobenzotrifluoride

HRID 1178203Notes

Reaction equation

HRID 1178203 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.CCOC(C)=O>C(Cl)(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

5

Reactant 3

HCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 5205973-Methoxy-5-nitrobenzotrifluoride

Product 1

HCID 27562513-Hydroxy-5-nitrobenzotrifluorideYield 42.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1-Methoxy-3-nitro-5-trifluoromethyl-benzene (3.5 g, 15.83 mmol) in 20 ml of CHCl3 was added a solution of 1M boron tribromide (23.74 ml, 23.74 mmol) and the reaction was stirred at RT for 3 days resulting in conversion to product by TLC (20% EtOAc:Hexanes). The reaction was partitioned between CH2Cl2/1N NaOH and extracted. The aqueous phase was acidified with 1N HCl and again extracted with CH2Cl2. The organics were dried over sodium sulfate and stripped down in vacuo giving 3-Nitro-5-trifluoromethyl-phenol (1.4 g, 6.76 mmol) as a yellow oil.

Workup

  1. customThe reaction was partitioned between CH2Cl2/1N NaOH
  2. extractionextracted
  3. extractionagain extracted with CH2Cl2
  4. dry with materialThe organics were dried over sodium sulfate

Sources & evidence

ORD record
ord-bbacc063bc684e079bf1db4fe00fc2b0
Source dataset
uspto-grants-2007_10
Patent number
US07276502B2

Reaction notes

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