Azobisisobutyronitrile → 2-(Bromomethyl)-5-fluorobenzo[d]thiazole

HRID 1772286Notes

Reaction equation

HRID 1772286 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([CH3:10])=[N:7][C:6]=2[CH:11]=1.C1C(=O)N([Br:19])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:19][CH2:10][C:8]1[S:9][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:11][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 5974375-Fluoro-2-methylbenzothiazole

Product 1

HCID 144586272-(Bromomethyl)-5-fluorobenzo[d]thiazoleYield 20.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 5-fluoro-2-methyl-1,3-benzothiazole (500 mg, 2.99 mmol), NBS (600 mg, 3.37 mmol) and AIBN (125 mg, 0.76 mmol) in carbon tetrachloride (25 ml) was heated at reflux for 20 hours under nitrogen with stirring. The solution was then concentrated to give a residue which was purified by silica gel column chromatography using 1% ethyl acetate in petroleum ether to afford 2-(bromomethyl)-5-fluoro-1,3-benzothiazole as a yellow solid (150 mg, 20%). 1H NMR (400 MHz, CDCl3): δ 7.81 (dd, J=8.8, 5.2 Hz, 1H), 7.70 (dd, J=9.2, 2.4 Hz, 1H), 7.23-7.16 (m, 1H), 4.80 (s, 2H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 hours under nitrogen
  3. concentrationThe solution was then concentrated
  4. customto give a residue which
  5. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-85c26036c76a4e469144f89b5d306f10
Source dataset
uspto-grants-2016_02
Patent number
US09249102B2

Reaction notes

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