Phosphorus tribromide → 3-(1-Bromoethyl)-4-(3-(dimethylamino)phenyl)-1H-isochromen-1-one

HRID 634389Notes

Reaction equation

HRID 634389 reaction equation
[CH3:1][N:2]([CH3:23])[C:3]1[CH:4]=[C:5]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[O:19])[O:11][C:10]=2[CH:20](O)[CH3:21])[CH:6]=[CH:7][CH:8]=1.P(Br)(Br)[Br:25]>C(Cl)Cl>[Br:25][CH:20]([C:10]1[O:11][C:12](=[O:19])[C:13]2[C:18]([C:9]=1[C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([N:2]([CH3:23])[CH3:1])[CH:4]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:21]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 1181312514-(3-(Dimethylamino)phenyl)-3-(1-hydroxyethyl)-1H-isochromen-1-one2×

Product 1

HCID 1181310563-(1-Bromoethyl)-4-(3-(dimethylamino)phenyl)-1H-isochromen-1-oneYield 125.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was made in a similar way as that of the intermediate C6, using 4-(3-(dimethylamino)phenyl)-3-(1-hydroxyethyl)-1H-isochromen-1-one (intermediate B8, 200 mg, 0.64 mmol), 1M PBr3 (1.1 ml, 1.1 mmol) in DCM (2 ml) at RT. The crude was purified with Biotage Silica SNAP 50 g with a gradient of DCM and MeOH to give the title compound (300 mg).

Workup

  1. customat RT
  2. customThe crude was purified with Biotage Silica SNAP 50 g with a gradient of DCM and MeOH

Sources & evidence

ORD record
ord-fc73e91ee2c049a188f70728e9ab0ae0
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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