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

HRID 2041218Notes

Reaction equation

HRID 2041218 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-94b9750b0db944a980c1313635c4ff93
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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