Phosphorus tribromide → 3-(1-Bromoethyl)-4-(4-(2-morpholinoethoxy)phenyl)-1H-isochromen-1-one hydrobromide

HRID 634396Notes

Reaction equation

HRID 634396 reaction equation
P(Br)(Br)[Br:2].O[CH:6]([C:8]1[O:9][C:10](=[O:33])[C:11]2[C:16]([C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[CH:20][CH:19]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:7]>C(Cl)Cl.CCOCC>[BrH:2].[Br:2][CH:6]([C:8]1[O:9][C:10](=[O:33])[C:11]2[C:16]([C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[CH:20][CH:19]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:7]

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 1181313013-(1-Hydroxyethyl)-4-(4-(2-morpholinoethoxy)phenyl)-1H-isochromen-1-one

Product 1

HCID 1181311493-(1-Bromoethyl)-4-(4-(2-morpholinoethoxy)phenyl)-1H-isochromen-1-one hydrobromideYield 61%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

1 M PBr3 in DCM (1.82 mL, 1.82 mmol) was added to 3-(1-hydroxyethyl)-4-(4-(2-morpholinoethoxy)phenyl)-1H-isochromen-1-one (Intermediate B15, 180 mg, 0.455 mmol) in DCM (2 ml) at RT. The reaction mixture was then was diluted with Et2O and filtered. The residue was further washed with Et2O and finally dried to give the title compound (150 mg, 61%) as a pink-red solid.

Workup

  1. filtrationfiltered
  2. washThe residue was further washed with Et2O
  3. customfinally dried

Sources & evidence

ORD record
ord-b53bff5770344fb19a4eb3142f39d834
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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