Phosphorus tribromide → 3-(1-bromoethyl)-4-(3,6-dihydro-2H-pyran-4-yl)-1H-isochromen-1-one

HRID 634400Notes

Reaction equation

HRID 634400 reaction equation
P(Br)(Br)[Br:2].[O:5]1[CH2:10][CH:9]=[C:8]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14](=[O:21])[O:13][C:12]=2[CH:22](O)[CH3:23])[CH2:7][CH2:6]1>C(Cl)Cl>[Br:2][CH:22]([C:12]1[O:13][C:14](=[O:21])[C:15]2[C:20]([C:11]=1[C:8]1[CH2:7][CH2:6][O:5][CH2:10][CH:9]=1)=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:23]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 1181310694-(3,6-Dihydro-2H-pyran-4-yl)-3-(1-hydroxyethyl)-1H-isochromen-1-one

Product 1

HCID 1181312613-(1-bromoethyl)-4-(3,6-dihydro-2H-pyran-4-yl)-1H-isochromen-1-oneYield 58.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1 M PBr3 in DCM (1.43 mL, 1.43 mmol) was added to 4-(3,6-dihydro-2H-pyran-4-yl)-3-(1-hydroxyethyl)-1H-isochromen-1-one (intermediate B18, 130 mg, 0.477 mmol) in DCM (2 mL) and stirred for 2 hrs at RT, then the reaction mixture was adsorbed on silica pad and straightforward purified on Biotage silica cartridge eluting with a gradient of hexane and AcOEt to give the title compound (94 mg, 58.7%) as an off white solid.

Workup

  1. customstraightforward purified on Biotage silica cartridge
  2. washeluting with a gradient of hexane and AcOEt

Sources & evidence

ORD record
ord-a44c95d25a634e07a67c62ac926209c5
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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