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

HRID 634384Notes

Reaction equation

HRID 634384 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:21]([Br:24])(Br)Br.OC[C:27]1[O:28][C:29](=[O:44])[C:30]2[C:35]([C:36]=1[C:37]1[CH:38]=[C:39]([CH3:43])[CH:40]=[CH:41][CH:42]=1)=[CH:34][CH:33]=[CH:32][CH:31]=2>CN(C=O)C>[Br:24][CH2:21][C:27]1[O:28][C:29](=[O:44])[C:30]2[C:35]([C:36]=1[C:37]1[CH:38]=[C:39]([CH3:43])[CH:40]=[CH:41][CH:42]=1)=[CH:34][CH:33]=[CH:32][CH:31]=2

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 1181311163-(Hydroxymethyl)-4-m-tolyl-1H-isochromen-1-one2×

Product 1

HCID 1181310793-(Bromomethyl)-4-m-tolyl-1H-isochromen-1-oneYield 73.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triphenylphosphine (270 mg, 1.030 mmol) and perbromomethane (342 mg, 1.030 mmol) were added to a solution of 3-(hydroxymethyl)-4-m-tolyl-1H-isochromen-1-one (intermediate B5, 211 mg, 0.792 mmol) in DMF (2 ml), and the resulting mixture was stirred at RT. The reaction was then purified via reverse phase chromatography with a Biotage C18 30 g SNAP column (Phase A, water 95%, ACN 4.5%, formic acid 0.5%; Phase B ACN 99.5%, formic acid 0.5%) to give the title compound (192 mg, 73.6%).

Workup

  1. customThe reaction was then purified via reverse phase chromatography with a Biotage C18 30 g SNAP column (Phase A, water 95%, ACN 4.5%, formic acid 0.5%; Phase B ACN 99.5%, formic acid 0.5%)

Sources & evidence

ORD record
ord-7aad7e9bfd2049d89a42b4de5629a22b
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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