Dichloromethane → 3-(1-Bromoethyl)-4-phenyl-1H-isochromen-1-one

HRID 634388Notes

Reaction equation

HRID 634388 reaction equation
O[CH:2]([C:4]1[O:5][C:6](=[O:20])[C:7]2[C:12]([C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH3:3].P(Br)(Br)[Br:22].C(Cl)Cl>>[Br:22][CH:2]([C:4]1[O:5][C:6](=[O:20])[C:7]2[C:12]([C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH3:3]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 24614Phosphorus tribromideHCID 1181311643-(1-Hydroxyethyl)-4-phenyl-1H-isochromen-1-one2×

Product 1

HCID 1181310753-(1-Bromoethyl)-4-phenyl-1H-isochromen-1-oneYield 51%

Procedure

The title compound was made in a similar way as that of the intermediate C6, using 3-(1-hydroxyethyl)-4-phenyl-1H-isochromen-1-one (Intermediate B1, 2.6 g, 9.76 mmol), 1M PBr3 in DCM (17.5 ml, 17.5 mmol) (30 ml) at RT. The crude was purified with Biotage Silica SNAP 100 g with a gradient of hexane and AcOEt to give the title compound (1.64 g, 51%).

Workup

  1. customat RT
  2. customThe crude was purified with Biotage Silica SNAP 100 g with a gradient of hexane and AcOEt

Sources & evidence

ORD record
ord-737944b38fc14387b9ffb9737755eae0
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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