Carbon tetrabromide → 3-Bromomethyl-4,6-dimethyl-benzo[d]isothiazole

HRID 2175180Notes

Reaction equation

HRID 2175180 reaction equation
[CH3:1][C:2]1[C:7]2[C:8]([CH2:11]O)=[N:9][S:10][C:6]=2[CH:5]=[C:4]([CH3:13])[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:34]>C(Cl)Cl>[Br:34][CH2:11][C:8]1[C:7]2[C:2]([CH3:1])=[CH:3][C:4]([CH3:13])=[CH:5][C:6]=2[S:10][N:9]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 58497417(4,6-Dimethyl-1,2-benzisothiazol-3-yl)-methanol

Product 1

HCID 584973913-Bromomethyl-4,6-dimethyl-benzo[d]isothiazoleYield 70.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4,6-dimethyl-benzo[d]isothiazol-3-yl)-methanol (100 mg, 0.5 mmol) in CH2Cl2 (15 mL) were added triphenylphosphine (PPh3) (200 mg, 0.78 mmol) and carbon tetrabromide (CBr4) (340 mg, 1 mmol) at room temperature. The solution was stirred at the same temperature for 1 hour. The solution was concentrated and the residue was purified by silica gel flash column chromatography with 10% EtOAc in Hexane as the eluent to afford the title compound (90 mg, 68%) as a white solid.

Workup

  1. concentrationThe solution was concentrated
  2. customthe residue was purified by silica gel flash column chromatography with 10% EtOAc in Hexane as the eluent

Sources & evidence

ORD record
ord-130485b7e1f84c17a437ca09de175ab3
Source dataset
uspto-grants-2015_06
Patent number
US09062056B2

Reaction notes

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