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

HRID 634386Notes

Reaction equation

HRID 634386 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]C(Br)(Br)Br.O[CH:26]([C:28]1[O:29][C:30](=[O:45])[C:31]2[C:36]([C:37]=1[C:38]1[CH:39]=[C:40]([CH3:44])[CH:41]=[CH:42][CH:43]=1)=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH3:27]>C(Cl)Cl>[Br:20][CH:26]([C:28]1[O:29][C:30](=[O:45])[C:31]2[C:36]([C:37]=1[C:38]1[CH:39]=[C:40]([CH3:44])[CH:41]=[CH:42][CH:43]=1)=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH3:27]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 1181312503-(1-Hydroxyethyl)-4-m-tolyl-1H-isochromen-1-one2×

Product 1

HCID 1181310323-(1-Bromoethyl)-4-m-tolyl-1H-isochromen-1-oneYield 18.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triphenylphosphine (365 mg, 1.39 mmol) and perbromomethane (461 mg, 1.39 mmol) were was added to a solution of 3-(1-hydroxyethyl)-4-m-tolyl-1H-isochromen-1-one (intermediate B6, 300 mg, 1.07 mmol) in DCM (2.2 ml), and the resulting mixture was stirred at RT. The reaction product was then purified on the silica Biotage SNAP 50 g, eluting with a gradient of hexane and EtOAc to give the title compound (67 mg, 18.3%).

Workup

  1. customThe reaction product was then purified on the silica Biotage SNAP 50 g
  2. washeluting with a gradient of hexane and EtOAc

Sources & evidence

ORD record
ord-3393616901124bd38bc1c01ece5f3e59
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

Loading…