N-bromobutanimide → Ethyl 5-bromo-4-(3-chloro-4-fluorophenyl)-1,3-thiazole-2-carboxylate

HRID 2038362Notes

Reaction equation

HRID 2038362 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[S:12][CH:13]=2)[CH:5]=[CH:6][C:7]=1[F:8].[Br:19]N1C(=O)CCC1=O>ClCCl.[Fe](Cl)(Cl)Cl>[Br:19][C:13]1[S:12][C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:10][C:9]=1[C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Cl:1])[CH:3]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 61385370Ethyl 4-(3-chloro-4-fluorophenyl)-1,3-thiazole-2-carboxylate

Product 1

HCID 70801639Ethyl 5-bromo-4-(3-chloro-4-fluorophenyl)-1,3-thiazole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 6344DichloromethaneSolvent

Procedure

1.94 g of the compound from Example 2A having a purity of 57% (3.87 mmol) are provided in 35 ml of dichloromethane, 6.04 g (33.9 mmol) of N-bromosuccinimide and a spatula tip of iron trichloride are added and the mixture is heated under reflux for 18 hours. The reaction mixture is concentrated, the residue is purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate 30:1), and 1.30 g (83% of theory) of the title compound are obtained.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 18 hours
  3. concentrationThe reaction mixture is concentrated
  4. customthe residue is purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate 30:1), and 1.30 g (83% of theory) of the title compound
  5. customare obtained

Sources & evidence

ORD record
ord-ce04511ec4f045cbb03e025b3bdae732
Source dataset
uspto-grants-2013_11
Patent number
US08575357B2

Reaction notes

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