Water → 1-(4-Bromophenoxy)-2-methylpropan-2-ol

HRID 57552

Reaction equation

HRID 57552 reaction equation
Cl[CH2:2][C:3]([CH3:6])([OH:5])[CH3:4].C([O-])([O-])=O.[K+].[K+].[Br:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.O>CN(C=O)C>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:2][C:3]([CH3:6])([OH:5])[CH3:4])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78084-Bromophenol2×HCID 11430Potassium CarbonateHCID 684091-Chloro-2-methylpropan-2-ol

Product 1

HCID 211863421-(4-Bromophenoxy)-2-methylpropan-2-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 1-chloro-2-methylpropan-2-ol (434.4 mg, 4 mmol) in DMF (10 mL) was added K2CO3 (552 mg, 4 mmol) and 4-bromophenol (346 mg, 2 mmol), the reaction was stirred at 140° C. for 48 hours. About of 10% 4-bromophenol was remained and the reaction was poured into 30 mL of water, extracted with EA (20 mL×3), washed with 30 mL of water and brine, concentrated and purified on TLC (EA:PE=1:3) to give yellow solid. MS (m/z): 196 (M−50)+

Workup

  1. extractionextracted with EA (20 mL×3)
  2. washwashed with 30 mL of water and brine
  3. concentrationconcentrated
  4. custompurified on TLC (EA:PE=1:3)
  5. customto give yellow solid

Sources & evidence

ORD record
ord-f38fff146e104ddebbca900c771cc61a
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Linked notes

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