Water → 6-Bromo-2-(2-fluoroethylthio)benzo[d]thiazole

HRID 1965858Notes

Reaction equation

HRID 1965858 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([SH:9])[S:8][C:4]=2[CH:3]=1.Br[CH2:13][CH2:14][F:15].C([O-])([O-])=O.[Cs+].[Cs+].O>CN1C(=O)CCC1>[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([S:9][CH2:13][CH2:14][F:15])[S:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 129822-Fluoroethyl bromideHCID 1785277616-Bromo-2-mercaptobenzothiazole

Product 1

HCID 592830416-Bromo-2-(2-fluoroethylthio)benzo[d]thiazoleYield 46.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To 6-bromobenzo[d]thiazole-2-thiol (160 mg, 0.65 mmol) and 1-bromo-2-fluoroethane (165 mg, 1.3 mmol) in 5 mL of NMP was added Cs2CO3 (635 mg, 1.95 mmol). The mixture was stirred at rt for 5 hours. It was added water (20 mL) and precipitate was collected through filtration and washed with water (10 mL) and dried under high vacuum. The crude product was purified with silica chromatography (5% to 30% EtOAc in hexane) to afford 6-Bromo-2-(2-fluoroethylthio)benzo[d]thiazole as a yellow solid (88 mg, 46%). MS (ESI) m/z 291.9, 293.9 (M+H+).

Workup

  1. filtrationwas collected through filtration
  2. washwashed with water (10 mL)
  3. customdried under high vacuum
  4. customThe crude product was purified with silica chromatography (5% to 30% EtOAc in hexane)

Sources & evidence

ORD record
ord-91826456b21c473e84620279e1a3d5b8
Source dataset
uspto-grants-2013_04
Patent number
US08420052B2

Reaction notes

Loading…