Dichloromethane → Ethyl 2-(bromomethyl)-1,3-thiazole-4-carboxylate

HRID 1792861Notes

Reaction equation

HRID 1792861 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([CH3:11])[S:9][CH:10]=1)=[O:5])[CH3:2].[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)Cl>ClCCCl>[Br:12][CH2:11][C:8]1[S:9][CH:10]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[N:7]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 293353Ethyl 2-methyl-1,3-thiazole-4-carboxylate

Product 1

HCID 11043146Ethyl 2-(bromomethyl)-1,3-thiazole-4-carboxylateYield 8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of ethyl-2-methylthiazole 4-carboxylate (500 mg, 2.9 mmol), N-bromosuccinimide (877 mg, 4.9 mmol), and benzoyl peroxide (5–10 mg) in 1,2-DCE (3 mL) was heated at 70° C. for 85 h. After cooling to room temperature, DCM (10 ml) was added and washed with water (3 times). The organic layer was dried over Na2SO4 and evaporated in vacuo. The residue was purified by preparative chromatography to yield the above-titled compound (58 mg). 1H NMR (CDCl3): 8.23 (1H, s), 4.77 (2H, s), 4.43 (2H, q), 1.42 (3H, t).

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with water (3 times)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customevaporated in vacuo
  5. customThe residue was purified by preparative chromatography

Sources & evidence

ORD record
ord-c368e0a839684f7b84c75961fa20ac31
Source dataset
uspto-grants-2006_07
Patent number
US07078420B2

Reaction notes

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