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

HRID 634387Notes

Reaction equation

HRID 634387 reaction equation
P(Br)(Br)[Br:2].[F:5][C:6]1[CH:7]=[C:8]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:22])[O:14][C:13]=2[CH:23](O)[CH3:24])[CH:9]=[CH:10][CH:11]=1>C(Cl)Cl>[Br:2][CH:23]([C:13]1[O:14][C:15](=[O:22])[C:16]2[C:21]([C:12]=1[C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([F:5])[CH:7]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:24]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 1181310784-(3-Fluorophenyl)-3-(1-hydroxyethyl)-1H-isochromen-1-one2×

Product 1

HCID 1181310803-(1-Bromoethyl)-4-(3-fluorophenyl)-1H-isochromen-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1 M PBr3 in DCM (2.3 ml, 2.332 mmol) was added to a solution of 4-(3-fluorophenyl)-3-(1-hydroxyethyl)-1H-isochromen-1-one (intermediate B7, 390 mg, 1.372 mmol) in DCM (7.8 ml) and the mixture stirred at RT for 2 hrs. The reaction mixture was then evaporated under reduced pressure and purified on a silica Biotage SNAP 100 g, eluting with a gradient of hexane and EtOAc to give the title (227 mg, 47.7%).

Workup

  1. customThe reaction mixture was then evaporated under reduced pressure
  2. custompurified on a silica Biotage SNAP 100 g
  3. washeluting with a gradient of hexane and EtOAc
  4. customto give the title (227 mg, 47.7%)

Sources & evidence

ORD record
ord-0617ccfdb1f741b2b36929452e54cbbf
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

Loading…