Hydrogen Bromide → 2-Bromo-4-(3-bromo-phenyl)-thiazole

HRID 1436368Notes

Reaction equation

HRID 1436368 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8](=O)[CH2:9][S:10][C:11]#[N:12])[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].[BrH:16]>C(O)(=O)C>[Br:16][C:11]1[S:10][CH:9]=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=2)[N:12]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 58961415HCID 58961415, compound

Product 1

HCID 689027322-Bromo-4-(3-bromo-phenyl)-thiazoleYield 83%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A suspension of 2-(3-bromophenyl)-2-oxoethyl thiocyanate (10.9075 g, 42.6 mmol), prepared in the previous step, in 64 mL of 30% hydrogen bromide in acetic acid was stirred under nitrogen at room temperature for 17 h. The yellow suspension was poured into 500 mL of 1 N NaOH (exotherm) and the mixture stirred at room temperature for 21 h. The solid present was collected by filtration, rinsed with water, ice-cold ethanol, hexane and then dried under high vacuum to give 2-bromo-4-(3-bromophenyl)-1,3-thiazole (11.3069 g, 83%) as a yellow solid, mp 88-90° C.; MS (ES) m/z 317.9 [M+H+].

Workup

  1. stirringthe mixture stirred at room temperature for 21 h
  2. filtrationThe solid present was collected by filtration
  3. washrinsed with water, ice-cold ethanol, hexane
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-5a5c7e3b50154d6eb7b92153ff68079c
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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