1-Bromopropane → 2-(3,5-Dimethyl-4-propoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 1690675Notes

Reaction equation

HRID 1690675 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([B:8]2[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH3:16])([CH3:15])[O:9]2)[CH:5]=[C:4]([CH3:17])[C:3]=1[OH:18].Br[CH2:20][CH2:21][CH3:22].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:17][C:4]1[CH:5]=[C:6]([B:8]2[O:12][C:11]([CH3:13])([CH3:14])[C:10]([CH3:16])([CH3:15])[O:9]2)[CH:7]=[C:2]([CH3:1])[C:3]=1[O:18][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 27346492,6-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Product 1

HCID 576184902-(3,5-Dimethyl-4-propoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture 2,6-Dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol (500 mg, 2.02 mmol, 1 eq.), 1-bromopropane (793 mg, 6.45 mmol, 3.2 eq.), and K2CO3 (334 mg, 2.42 mmol, 1.2 eq.) in acetone (20 mL) is heated at 65° C. for 4 days. After cooling to room temperature, the reaction is concentrated, diluted with EtOAc and sequentially washed with H2O and saturated aqueous NaCl. The organic solution is dried over Na2SO4 and concentrated to give 2-(3,5-Dimethyl-4-propoxy-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane as a clear oil.

Workup

  1. concentrationthe reaction is concentrated
  2. additiondiluted with EtOAc
  3. washsequentially washed with H2O and saturated aqueous NaCl
  4. dry with materialThe organic solution is dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2d6f8e605e434f208aef6342a71d9c6a
Source dataset
uspto-grants-2012_04
Patent number
US08153671B2

Reaction notes

Loading…