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

HRID 634382Notes

Reaction equation

HRID 634382 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:21][C:22]1[O:23][C:24](=[O:38])[C:25]2[C:30]([C:31]=1[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[CH:29][CH:28]=[CH:27][CH:26]=2.[Br:39]C(Br)(Br)Br.C(Cl)Cl>CO>[Br:39][CH2:21][C:22]1[O:23][C:24](=[O:38])[C:25]2[C:30]([C:31]=1[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[CH:29][CH:28]=[CH:27][CH:26]=2

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 214632763-(Hydroxymethyl)-4-phenyl-1H-isochromen-1-one2×

Product 1

HCID 1181311893-(Bromomethyl)-4-phenyl-1H-isochromen-1-oneYield 47.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Triphenylphosphine (250 mg, 0.953 mmol) was added to a solution of 3-(hydroxymethyl)-4-phenyl-1H-isochromen-1-one (intermediate B2, 185 mg, 0.733 mmol) and perbromomethane (316 mg, 0.953 mmol) in DCM (3.7 ml, 57.5 mmol), and the resulting mixture was stirred at RT for 3 days, adding the reagents several times to achieve completion (overall 4 equivalents). The reaction was taken up with MeOH then concentrated under reduced pressure. The crude was purified over a Biotage Silica 50 g SNAP cartridge with a gradient of hexane and EtOAc to give the title compound (0.11 g, 47.6%).

Workup

  1. additionadding the reagents several times
  2. concentrationthen concentrated under reduced pressure
  3. customThe crude was purified over a Biotage Silica 50 g SNAP cartridge with a gradient of hexane and EtOAc

Sources & evidence

ORD record
ord-0b541681469a4db998906f02d996a19b
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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