Reaction #1265385

Reaction equation

EtOAc

1-Methoxy-3-nitro-5-trifluoromethyl-benzene

boron tribromide

→

3-Nitro-5-trifluoromethyl-phenol

Yield 42.7%

Solvents

—

Hexanes

CHCl3

Conditions

Workup

1. 1
   OtherThe reaction was partitioned between CH2Cl2/1N NaOH
2. 2
   Extractionextracted
3. 3
   Extractionagain extracted with CH2Cl2
4. 4
   DryingThe organics were dried over sodium sulfate

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.

Source