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

HRID 1747455Notes

Reaction equation

HRID 1747455 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.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=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-1,2-benzisothiazol-3-yl)-methanol (100 mg, 0.5 mmol) in CH2Cl2 (15 mL) were added PPh3 (200 mg, 0.78 mmol) and 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 CombiFlash with 10% EtOAc in Hexane as the eluent to afford the desirable product 3-Bromomethyl-4,6-dimethyl-1,2-benzisothiazole (90 mg, 68%) as a white solid.

Workup

  1. concentrationThe solution was concentrated
  2. customthe residue was purified by CombiFlash with 10% EtOAc in Hexane as the eluent

Sources & evidence

ORD record
ord-fb7c3f7c4b7a45a1b053eaf814ea0ee8
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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