Tert-Butylamine → 2-Bromo-4,6-dichlorophenol

HRID 2046561Notes

Reaction equation

HRID 2046561 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].[Br:10]Br.C(N)(C)(C)C>C1(C)C=CC=CC=1>[Br:10][C:4]1[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[C:3]=1[OH:9]

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 84492,4-DichlorophenolHCID 24408Bromine

Product 1

HCID 206172-Bromo-4,6-dichlorophenolYield 467.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-50 °C

Procedure

To a solution of 2,4-dichloro-phenol (15 g, 19.02 mmol) in toluene (200 ml) was added bromine (5.1 ml, 184.04 mmol) dropwise at −50° C. Then, tert-butylamine (19.4 ml, 99.02 mmol) was added dropwise and the reaction mixture was stirred at −50° C. for 30 minutes. The reaction was quenched by addition of 38% aqueous NaHSO3 solution, the organic layer was separated and the aqueous layer was extracted two times with EtOAc. The combined organic extracts were dried with Na2SO4, filtered and evaporated to obtain the title compound (21.5 g, 96%) as white solid.

Workup

  1. customThe reaction was quenched by addition of 38% aqueous NaHSO3 solution
  2. customthe organic layer was separated
  3. extractionthe aqueous layer was extracted two times with EtOAc
  4. dry with materialThe combined organic extracts were dried with Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-dfd8578ee80d4fbf8584b402787dbdb3
Source dataset
uspto-grants-2013_11
Patent number
US08592426B2

Reaction notes

Loading…