Isobutylene oxide → 1-(4-Bromo-2-methoxyphenoxy)-2-methylpropan-2-ol

HRID 1044406Notes

Reaction equation

HRID 1044406 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([O:9][CH3:10])[CH:3]=1.[CH3:11][C:12]1([CH3:15])[CH2:14][O:13]1.C(=O)([O-])[O-].[K+].[K+].P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+]>C(#N)C.CCOCC.CCOC(C)=O.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:11][C:12]([CH3:15])([OH:13])[CH3:14])=[C:4]([O:9][CH3:10])[CH:3]=1

Participants

9

Reactant 4

HCID 11208Isobutylene oxideHCID 11430Potassium CarbonateHCID 24243Trisodium PhosphateHCID 2622344-Bromo-2-methoxyphenol

Product 1

HCID 595950491-(4-Bromo-2-methoxyphenoxy)-2-methylpropan-2-olYield 92.1%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-bromo-2-methoxyphenol (8 g, 39.4 mmol), 2,2-dimethyloxirane (14 mL, 158 mmol), potassium carbonate (4.3 g, 35.5 mmol), and sodium phosphate, monobasic (4.25 g, 35.5 mmol) in acetonitrile and water (85:15, 100 mL) was stirred in a steel bomb at 150-165° C. for 8 h. The reaction was cooled to RT, diluted with ether and EtOAc (1:1), washed with 1N NaOH, dried (Na2SO4), and concentrated. The crude was passed through a pad of silica gel using EtOAc for elution to afford the desired product 1-(4-bromo-2-methoxyphenoxy)-2-methylpropan-2-ol 9A (10 g, 36.3 mmol, 92% yield) as a brown oil. 1H NMR (400 MHz, Chloroform-d) δ6.95-7.08 (2H, m), 6.77 (1H, d, J=8.28 Hz), 3.85 (3H, s), 3.79 (2H, s), 1.34 (6H, s).

Workup

  1. washwashed with 1N NaOH
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. washfor elution

Sources & evidence

ORD record
ord-9121703c7ed543eab7622c8c1dfd3050
Source dataset
uspto-grants-2013_10
Patent number
US08563583B2

Reaction notes

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