2-Isopropylphenol → 4-Bromo-2-(propan-2-yl)phenol

HRID 25823

Reaction equation

HRID 25823 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([CH3:3])[CH3:2].[Br-:11].[Br-].O1CCOCC1>CCOCC>[Br:11][C:8]1[CH:7]=[CH:6][C:5]([OH:10])=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:9]=1

Participants

4

Reactant 2

HCID 69432-IsopropylphenolHCID 222259191,4-Dioxane dibromide

Product 1

HCID 147934824-Bromo-2-(propan-2-yl)phenolYield 66%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2-isopropylphenol (12) (2.0 g, 14.6 mmol) in 15 ml of Et2O at 0° C. was added dioxane dibromide (3.62 g, 14.6 mmol, 1 eqv). The, solution was allowed to stir for 30 min at rt. The reaction mixture was washed with sat. NaCl and 10% NaHCO3. The Et2O phase was concentrated in vacuo and then vacuum distilled (142-145° C., 20 mm Hg) to yield 2.07 g of a clear oil (66%) which solidified upon standing: 1H NMR (500 MHz, CDCl3) δ 1.23 (d, J=3.7 Hz, 6H), 3.16 (m, 1H), 4.84 (s, 1H), 6.61 (d, J=8.6 Hz, 1H), 7.15 (d, J=11.0 Hz, 1H), 7.28 (s, 1H); 13C NMR (125 MHz, CDCl3) δ 22.33, 27.17, 113.24, 116.99, 129.34, 129.50, 136.91, 151.81; LRMS (EI) (M+, 214/216).

Workup

  1. washThe reaction mixture was washed with sat. NaCl and 10% NaHCO3
  2. concentrationThe Et2O phase was concentrated in vacuo
  3. distillationvacuum distilled (142-145° C., 20 mm Hg)

Sources & evidence

ORD record
ord-bb4dddf33ec0478c97b085a49a045d32
Source dataset
uspto-grants-2005_02
Patent number
US06858600B2

Linked notes

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