반응 #487535

반응 방정식

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

PCC

→

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

용매

dichloromethane

반응 조건

후처리

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

실험 절차

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%).

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