Water → 4'-Bromophenacyl thiocyanate

HRID 1992553Notes

Reaction equation

HRID 1992553 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1)=[O:4].[S-:12][C:13]#[N:14].[K+].O>C(O)C>[Br:11][C:8]1[CH:9]=[CH:10][C:5]([C:3](=[O:4])[CH2:2][S:12][C:13]#[N:14])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 74544-Bromophenacyl bromideHCID 516872Potassium thiocyanate

Product 1

HCID 2449684'-Bromophenacyl thiocyanateYield 98.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2,4′-dibromoacetophenone (56.08 g, 0.20 mol) and potassium thiocyanate (21.57 g, 0.22 mol) in 1 L of absolute ethanol was stirred under nitrogen at room temperature for 5 h. The reaction was added to 2 L of water and the mixture stirred at room temperature for 2 h. The solid present was collected by filtration, rinsed with water, ice-cold ethanol, hexane, and then dried under high vacuum to give 2-(4-bromophenyl)-2-oxoethyl thiocyanate (50.39 g, 98%) as a white solid, mp 148-149° C.

Workup

  1. stirringthe mixture stirred at room temperature for 2 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-325cffdb8d10498a90939946d4d40d68
Source dataset
uspto-grants-2010_01
Patent number
US07649007B2

Reaction notes

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