2-Bromophenol → HCID 60880657, compound

HRID 528654Notes

Reaction equation

HRID 528654 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].Cl[CH2:10][C:11]([CH3:14])([OH:13])[CH3:12].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:10][C:11]([CH3:14])([OH:13])[CH3:12]

Participants

6

Reactant 3

HCID 72442-BromophenolHCID 10340Sodium CarbonateHCID 684091-Chloro-2-methylpropan-2-ol

Product 1

HCID 60880657HCID 60880657, compoundYield 64.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-bromophenol (3.0 g, 1.745 mmol, Aldrich) and 1-chloro-2-methylpropan-2-ol (2.8 g, 6.397 mmol, Spectrochem) in DMF (15 mL) was added sodium carbonate (1.23 g, 11.63 mmol). The reaction mixture was heated at 90° C. for 12 h. After completion, the reaction mixture was diluted with water (10 mL) and extracted with ethyl acetate (2×50 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain crude material that was purified by combiflash silica gel column chromatography (column size: 12 g; elution: 0-5% ethyl acetate in hexane) to yield 1-(2-bromophenoxy)-2-methylpropan-2-ol (2.7 mg, 64.2%) as a transparent liquid. m/z (ESI) 243.3 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto obtain crude material that
  5. customwas purified by combiflash silica gel column chromatography (column size: 12 g; elution: 0-5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-3a44120d318c412ca92ef80317e0b6f0
Source dataset
uspto-grants-2016_05
Patent number
US09346798B2

Reaction notes

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