Pinacol → 4-Chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

HRID 1469377Notes

Reaction equation

HRID 1469377 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[B:9]([OH:11])[OH:10].O[C:13]([C:16](O)([CH3:18])[CH3:17])([CH3:15])[CH3:14]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[B:9]1[O:10][C:16]([CH3:18])([CH3:17])[C:13]([CH3:15])([CH3:14])[O:11]1

Participants

4

Reactant 2

HCID 6425PinacolHCID 441193422-Chloro-5-hydroxybenzeneboronic acid

Product 1

HCID 534868364-Chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolYield 83%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

2-chloro-5-hydroxyphenyl boronic acid (409 mg, 2.37 mmol), pinacol (336 mg, 2.85 mmol), toluene (20 ml) and 4 angstrom molecular sieves (400 mg) were combined and heated at 120° C. for 2 h. The reaction mixture was allowed to cool and was then partitioned between EtOAc (2×30 ml) and water (30 ml). The combined organics were washed with brine (20 ml), dried (Na2SO4) and evaporated in vacuo to afford the desired product as a white solid (500 mg, 83%).

Workup

  1. temperatureto cool
  2. customwas then partitioned between EtOAc (2×30 ml) and water (30 ml)
  3. washThe combined organics were washed with brine (20 ml)
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-504b09715ecb4483913593e7ab16a9e2
Source dataset
uspto-grants-2015_04
Patent number
US09006269B2

Reaction notes

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