Reaction #487535

Reaction equation

(3-bromo-4-((5-phenylpentyl)amino)phenyl)methanol

PCC

→

3-bromo-4-((5-phenylpentyl)amino)benzaldehyde

Solvents

dichloromethane

Conditions

Workup

1. 1
   ConcentrationThe mixture was concentrated
2. 2
   Otherpurified by chromatography on silica gel (ethyl acetate-hexane)

Procedure

A solution of 5-bromopentylbenzene [14469-83-1](4 g, 17.6 mmol) in HMPA (55 g) was treated with 4-amino-3-bromobenzemethanol [146019-46-7] and dry K2CO3 (4.87 g, 35.2 mmol) for ˜18 h at 120° C. The mixture was cooled to rt, poured onto water (600 mL) and extracted with ethyl acetate (200 mL). The organic phase was washed with water (200 mL), dried over Na2SO4, concentrated, and purified by chromatography (ethyl acetate/hexane) to give (3-bromo-4-((5-phenylpentyl)amino)phenyl)methanol (2.24 g, 37%). A solution of (3-bromo-4-((5-phenylpentyl)amino)phenyl)methanol (8.0 g, 23 mmol) in dichloromethane (160 mL) was treated with silica gel (24 g) and PCC (14.9 g, 69 mmol) at rt for ˜18 h. The mixture was concentrated, and purified by chromatography on silica gel (ethyl acetate-hexane) to give 3-bromo-4-((5-phenylpentyl)amino)benzaldehyde Intermediate-21 (3.5 g, 44%).

Source