Hydrogen Bromide → 2-Bromo-4-(4-bromophenyl)thiazole

HRID 493969Notes

Reaction equation

HRID 493969 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][S:10][C:11]#[N:12])=[CH:4][CH:3]=1.[OH-].[Na+].[BrH:16]>C(O)(=O)C>[Br:16][C:11]1[S:10][CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)[N:12]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 2449684'-Bromophenacyl thiocyanate

Product 1

HCID 685381612-Bromo-4-(4-bromophenyl)thiazoleYield 84%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A suspension of 2-(4-bromophenyl)-2-oxoethyl thiocyanate (5.12 g, 20.0 mmol), prepared in the previous step, in 30 mL of 30% hydrogen bromide in acetic acid was stirred under nitrogen at room temperature for 7 h. The yellow suspension was poured into 200 mL of 1 N NaOH (exotherm) and the mixture stirred at room temperature for 17 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-(4-bromophenyl)-1,3-thiazole (5.36 g, 84%) as a light yellow solid, mp 117-119° C.; MS (ES) m/z 318/320/322 [M+H]+.

Workup

  1. stirringthe mixture stirred at room temperature for 17 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-5ce104683f014a7eaa971e251658692e
Source dataset
uspto-grants-2009_05
Patent number
US07538107B2

Reaction notes

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