Dichloromethane → 3-(Bromomethyl)-4-(2-fluorophenyl)-1H-isochromen-1-one

HRID 634383Notes

Reaction equation

HRID 634383 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30](=[O:37])[O:29][C:28]=1[CH2:38]O.[Br:40]C(Br)(Br)Br.C(Cl)Cl>CO>[Br:40][CH2:38][C:28]1[O:29][C:30](=[O:37])[C:31]2[C:36]([C:27]=1[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[F:20])=[CH:35][CH:34]=[CH:33][CH:32]=2

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 1181313584-(2-Fluorophenyl)-3-(hydroxymethyl)-1H-isochromen-1-one2×

Product 1

HCID 1181312733-(Bromomethyl)-4-(2-fluorophenyl)-1H-isochromen-1-oneYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Triphenylphosphine (0.127 g, 0.488 mmol)) was added to a solution of 4-(2-fluorophenyl)-3-(hydroxymethyl)-1H-isochromen-1-one (intermediate B4, 40 mg, 0.148 mmol) and perbromomethane (0.161 g, 0.488 mmol) in DCM (0.7 ml, 57.5 mmol), and the resulting mixture was stirred at RT for 24 hrs. The reaction was taken up with MeOH then concentrated under reduced pressure. The crude was purified over a Biotage Silica 10 g SNAP cartridge with a gradient of hexane and EtOAc to give the title compound (37 mg, 75%).

Workup

  1. concentrationthen concentrated under reduced pressure
  2. customThe crude was purified over a Biotage Silica 10 g SNAP cartridge with a gradient of hexane and EtOAc

Sources & evidence

ORD record
ord-054bf81ecc5e49be84520df377826cd7
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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