N-bromobutanimide → Tert-butyl 5-(bromomethyl)-2-phenylthiazole-4-carboxylate

HRID 1799100Notes

Reaction equation

HRID 1799100 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].[Br:20]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:20][CH2:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 67424508Tert-butyl 5-methyl-2-phenylthiazole-4-carboxylate

Product 1

HCID 67424804Tert-butyl 5-(bromomethyl)-2-phenylthiazole-4-carboxylateYield 75%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of tert-butyl 5-methyl-2-phenylthiazole-4-carboxylate (1.0 g 3.64 mmol), N-bromosuccinimide (NBS) (0.65 g 3.64 mmol), and benzoyl peroxide (BPO) (5.5 mg, 0.023 mmol) in CCl4 (30 ml) was heated at reflux for 16 h. The reaction mixture was concentrated in vacuo and purified by flash chromatography to give tert-butyl 5-(bromomethyl)-2-phenylthiazole-4-carboxylate as a light yellow solid (0.96 g, 75% yield).

Workup

  1. temperatureat reflux for 16 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-e8a0eca3991041818a64f2537b32f019
Source dataset
uspto-grants-2013_01
Patent number
US08343997B2

Reaction notes

Loading…