4-Bromophenol → 3-(4-Bromophenoxy)propan-1-ol
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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, 2H), 6.84 (d, 2H), 4.05 (t, 2H), 3.72 (t, 2H), 1.96 (m, 2H).