Tert-Butylamine → 2-Bromo-5-phenoxyphenol

HRID 1289180Notes

Reaction equation

HRID 1289180 reaction equation
C(N)(C)(C)C.[Br:6]Br.[O:8]([C:15]1[CH:16]=[C:17]([OH:21])[CH:18]=[CH:19][CH:20]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1(C)C=CC=CC=1.C(Cl)Cl>[Br:6][C:18]1[CH:19]=[CH:20][C:15]([O:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:16][C:17]=1[OH:21]

Participants

6

Reactant 3

HCID 6385Tert-ButylamineHCID 128423-PhenoxyphenolHCID 24408Bromine

Product 1

HCID 189257712-Bromo-5-phenoxyphenolYield 26.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-70 °C

Procedure

To a solution of t-butylamine (1.1 ml, 10.7 mmol) in 13 ml toluene, cooled to -30° C. was added bromine (0.28 ml, 5.35 mmol). The mixture was cooled to -70° C. and was treated with 3-phenoxyphenol (2.0 g, 10.7 mmol) dissolved in 2 ml CH2Cl2. The reaction was stirred to ambient temperature over 5 h, quenched with water and diluted with CH2Cl2. The organic phase was washed with water and brine and dried over Na2SO4. Column chromatography (SiO2 ; 5:95 EtOAc/Hex) afforded 380 mg (14%) of 2-bromo-5-phenoxyphenol.

Workup

  1. customquenched with water
  2. additiondiluted with CH2Cl2
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-b28e568f9c23497799597867df32367c
Source dataset
uspto-grants-1998_05
Patent number
US05747540

Reaction notes

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