Hydrogen Bromide → 2-Bromo-4-(4-bromo-2-fluorophenyl)-1,3-thiazole

HRID 1436413Notes

Reaction equation

HRID 1436413 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][S:10][C:11]#[N:12])=[C:4]([F:14])[CH:3]=1.[OH-].[Na+].O.[BrH:18]>C(O)(=O)C>[Br:18][C:11]1[S:10][CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=2[F:14])[N:12]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 962WaterHCID 14798Sodium HydroxideHCID 866186052-(4-Bromo-2-fluorophenyl)-2-oxoethyl thiocyanate

Product 1

HCID 689032302-Bromo-4-(4-bromo-2-fluorophenyl)-1,3-thiazoleYield 98%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-(4-Bromo-2-fluorophenyl)-2-oxoethyl thiocyanate (2.1 g, 7.6 mmol), prepared in the previous step, in 15 mL of 33% hydrogen bromide in acetic acid was stirred overnight. The reaction was neutralized with 60 mL of 2N NaOH and 60 mL of water. The resulting residue was collected by suction filtration and placed under high vacuum to give 2.6 g of a brown paste. The crude product was purified on silica gel using a stepwise gradient of 5-20% ethyl acetate:hexane to give 2-bromo-4-(4-bromo-2-fluorophenyl)-1,3-thiazole (2.5 g, 98%), MS (ES) m/z 338 [M+H]+.

Workup

  1. filtrationThe resulting residue was collected by suction filtration
  2. customto give 2.6 g of a brown paste
  3. customThe crude product was purified on silica gel using a stepwise gradient of 5-20% ethyl acetate

Sources & evidence

ORD record
ord-a099271f3ea3498693eb02b1db1b3ff6
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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