Reaction #1596945

Reaction equation

2-(4-benzyloxy-3-fluorophenyl)-4-bromo-5-propyltetrahydropyran

triethylamine

→

2-fluoro-4-(5-propyltetrahydropyran-2-yl)phenol

Solvents

MTBE

toluene water

Conditions

Workup

1. 1
   Otherthe organic phase is separated off
2. 2
   ExtractionThe aqueous phase is extracted with MTBE
3. 3
   WashThe combined organic phases are washed with water
4. 4
   Otherdried
5. 5
   ConcentrationThe solution is concentrated to dryness
6. 6
   Otherthe residue is used directly for the following reaction

Procedure

123.0 g (0.30 mol) of 2-(4-benzyloxy-3-fluorophenyl)-4-bromo-5-propyltetrahydropyran are hydrogenated in toluene/water in the presence of Pd/C (5% of Pd) and 86.0 ml (0.60 mol) of triethylamine. The reaction solution is diluted with MTBE, and the organic phase is separated off. The aqueous phase is extracted with MTBE. The combined organic phases are washed with water and dried using sodium sulfate. The solution is concentrated to dryness, and the residue is used directly for the following reaction.

Source