Carbon Tetrachloride → 2-Benzyl-6-bromomethyl-benzothiazole

HRID 911330Notes

Reaction equation

HRID 911330 reaction equation
[CH2:1]([C:8]1[S:9][C:10]2[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:11]=2[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C(=O)N([Br:25])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C.C(Cl)(Cl)(Cl)Cl>C(Cl)(Cl)Cl>[CH2:1]([C:8]1[S:9][C:10]2[CH:16]=[C:15]([CH2:17][Br:25])[CH:14]=[CH:13][C:11]=2[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 508498892-Benzyl-6-methyl-benzothiazole

Product 1

HCID 576565502-Benzyl-6-bromomethyl-benzothiazoleYield 69%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Combine 2-benzyl-6-methyl-benzothiazole (0.6 g, 2.51 mmol), NBS (0.5 g, 2.63 mmol), AIBN (40 mg, 0.25 mmol), carbon tetrachloride (10 mL) and reflux for 3 h. Cool the reaction mixture to ambient temperature, dilute with chloroform and wash with water. Dry the combined organic extracts over anhydrous Na2SO4, evaporate the solvent and purify by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 9:1) to obtain the title compound as a white solid (0.2 g, 69%). MS (ES+) m/z: 319 (M+H)+.

Workup

  1. washwash with water
  2. dry with materialDry the combined organic extracts over anhydrous Na2SO4
  3. customevaporate the solvent
  4. custompurify by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 9:1)

Sources & evidence

ORD record
ord-7a0dbd793abd41c6834be887afbe26d3
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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