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

HRID 1404550Notes

Reaction equation

HRID 1404550 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 as white solid (21.5 g, 96%).

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-980b675e45254fd48fb6208ed927556a
Source dataset
uspto-grants-2014_12
Patent number
US08912221B2

Reaction notes

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