4-Bromophenol → 3-(4-Bromophenoxy)propan-1-ol

HRID 1054640Notes

Reaction equation

HRID 1054640 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Br[CH2:10][CH2:11][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][CH2:11][CH2:12][OH:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 78084-BromophenolHCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanol

Product 1

HCID 187610183-(4-Bromophenoxy)propan-1-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-bromophenol (10 g, 58 mmol) in DMF (10 mL) was added 3-bromopropan-1-ol (9.6 g, 69 mmol) and potassium carbonate (13.6 g, 98 mmol). The mixture was stirred at room temperature for 12 h. LCMS showed the reaction was almost complete. The mixture was partitioned between water and ethyl acetate (20 mL×3), The combined organics were dried and concentrated to give the title compound that was used in the next step without further purification (14.7 g, quant). 1H NMR (400 MHz, CD3OD) δ 7.36 (d, 2 H), 6.84 (d, 2 H), 4.05 (t, 2 H), 3.72 (t, 2 H), 1.96 (m, 2 H).

Workup

  1. customThe mixture was partitioned between water and ethyl acetate (20 mL×3)
  2. customThe combined organics were dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e6802b0d9de4438dac6705058333fa11
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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