(3-Bromo-4-((5-phenylpentyl)amino)phenyl)methanol → 3-Bromo-4-((5-phenylpentyl)amino)benzaldehyde

HRID 72101Notes

Reaction equation

HRID 72101 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:20][OH:21])[CH:5]=[CH:6][C:7]=1[NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH:20]=[O:21]

Participants

4

Reactant 2

HCID 86687855(3-Bromo-4-((5-phenylpentyl)amino)phenyl)methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 866878543-Bromo-4-((5-phenylpentyl)amino)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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%).

Workup

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

Sources & evidence

ORD record
ord-b1230d7e08064fa8a56efb51f278f178
Source dataset
uspto-grants-2014_09
Patent number
US08828973B2

Reaction notes

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