Carbon tetrabromide → 3-(Bromomethyl)-4-(3-fluorophenyl)-1H-isochromen-1-one

HRID 634385Notes

Reaction equation

HRID 634385 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:21]([Br:24])(Br)Br.[F:25][C:26]1[CH:27]=[C:28]([C:32]2[C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[C:35](=[O:42])[O:34][C:33]=2CO)[CH:29]=[CH:30][CH:31]=1>C(Cl)Cl.CO>[Br:24][CH2:21][C:33]1[O:34][C:35](=[O:42])[C:36]2[C:41]([C:32]=1[C:28]1[CH:29]=[CH:30][CH:31]=[C:26]([F:25])[CH:27]=1)=[CH:40][CH:39]=[CH:38][CH:37]=2

Participants

6

Reactant 3

HCID 11205Carbon tetrabromide2×HCID 11776Triphenylphosphine2×HCID 1181311434-(3-Fluorophenyl)-3-(hydroxymethyl)-1H-isochromen-1-one2×

Product 1

HCID 1181312373-(Bromomethyl)-4-(3-fluorophenyl)-1H-isochromen-1-oneYield 59.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Triphenylphosphine (265 mg, 1.01 mmol) and perbromomethane (335 mg, 1.010 mmol) were added to a solution of 4-(3-fluorophenyl)-3-(hydroxymethyl)-1H-isochromen-1-one (intermediate B3, 210 mg, 0.777 mmol) in DCM (6.5 ml) and the mixture was stirred overnight at RT. Further triphenylphosphine (265 mg, 1.010 mmol) and perbromomethane (335 mg, 1.01 mmol) were then added and left on stirring at RT for 6 hrs. The reaction was then diluted with MeOH (1 ml) and straightforward purified on 50 g Biotage silica cartridge eluting with a gradient of Hexane and EtOAc to give the title compound (154 mg, 59.5%) as a yellow solid.

Workup

  1. waitleft
  2. stirringon stirring at RT for 6 hrs
  3. customstraightforward purified on 50 g Biotage silica cartridge
  4. washeluting with a gradient of Hexane and EtOAc

Sources & evidence

ORD record
ord-ff10da16e5794b8fa07b8535e29bd4f2
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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