4-Bromophenol → HCID 54570022, compound

HRID 338281Notes

Reaction equation

HRID 338281 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Br[CH2:10][C:11]([CH3:15])([CH3:14])[CH2:12][OH:13].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:10][C:11]([CH3:15])([CH3:14])[CH2:12][OH:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 78084-BromophenolHCID 11430Potassium CarbonateHCID 1425013-Bromo-2,2-dimethyl-1-propanol

Product 1

HCID 54570022HCID 54570022, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 4-bromophenol (300 mg, 1.74 mmol) in DMF (10 mL) was added 3-bromo-2,2-dimethylpropan-1-ol (579 mg, 3.47 mmol) and potassium carbonate (720 mg, 5.22 mmol). The mixture was degassed with nitrogen three times and heated to 90° C. for 48 h. The mixture was cooled to room temperature and then filtered. The filtrate was concentrated in vacuo to give a residue, which was purified by flash chromatography (EtOAc/petroleum ether=1:10 to 1:1) to give 3-(4-bromophenoxy)-2,2-dimethylpropan-1-ol (130 mg, 29%) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.37 (d, 2H), 6.79 (d, 2H), 3.73 (s, 2H), 3.54 (s, 2H), 1.02 (s, 6H).

Workup

  1. customThe mixture was degassed with nitrogen three times
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customto give a residue, which
  6. customwas purified by flash chromatography (EtOAc/petroleum ether=1:10 to 1:1)

Sources & evidence

ORD record
ord-be7c10b017f94d9f901f69f8d4687288
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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