5-Bromo-2-methylbenzothiazole → 5-Bromo-2-(bromomethyl)-1,3-benzothiazole

HRID 1487465Notes

Reaction equation

HRID 1487465 reaction equation
[Br: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.[Br:12]NC(=O)CCC(N)=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([CH2:10][Br:12])=[N:7][C:6]=2[CH:11]=1

Participants

5

Reactant 2

HCID 30174575-Bromo-2-methylbenzothiazoleHCID 9834204N-Bromosuccinamide

Product 1

HCID 144586425-Bromo-2-(bromomethyl)-1,3-benzothiazoleYield 63.1%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 5-Bromo-2-methyl-benzothiazole (1.0 g, 4.385 mmol) in CCl4 (15 mL) is added N-bromosuccinamide (1.1 g, 6.140 mmol) and azobisisobutyronitrile (0.029 g, 0.175 mmol) at room temperature reaction. The reaction mixture is heated to 75° C. for 16 hours. Reaction mixture is cooled to room temperature, filtered and the solvent evaporated in vacuo to give the crude material, which is then purified by flash chromatography using 3.5% ethyl acetate in hexane as an eluent to afford the title compound (0.85 g). 1H NMR (400 MHz, DMSO-d6) δ: 5.12 (s, 2H), 7.68-7.71 (dd, J1=1.92 Hz, J2=8.76 Hz, 1H), 7.95 (d, J=8.6 Hz, 1H), 8.43 (d, J=1.92 Hz, 1H). LC-MS (m/z): [M+H]=308.2.

Workup

  1. customreaction
  2. customReaction mixture
  3. temperatureis cooled to room temperature
  4. filtrationfiltered
  5. customthe solvent evaporated in vacuo
  6. customto give the crude material, which
  7. customis then purified by flash chromatography

Sources & evidence

ORD record
ord-2778deacac824ae6ac0d5c14afa2258f
Source dataset
uspto-grants-2016_08
Patent number
US09428528B2

Reaction notes

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