Pinacol → 2-[5-Chloro-2-(phenylmethoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 16097

Reaction equation

HRID 16097 reaction equation
[OH:1][C:2]([C:5]([OH:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:14]([B:16](O)O)[CH:15]=1>C(OCC)C>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[C:14]([B:16]2[O:8][C:5]([CH3:7])([CH3:6])[C:2]([CH3:4])([CH3:3])[O:1]2)[CH:15]=1

Participants

4

Reactant 2

HCID 6425Pinacol2×HCID 41987402-Benzyloxy-5-chlorobenzeneboronic acid

Product 1

HCID 672777732-[5-Chloro-2-(phenylmethoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Pinacol (3.24 g) was added to a solution of [5-chloro-2-(phenylmethoxy)phenyl]-boronic acid (6 g) in diethyl ether, and stirred for 24 h. 4 A molecular sieves and pinacol (1.5 g) were added, stirred for a further 24 h. The sieves were filtered and the filtrate was washed with water and brine, then dried (MgSO4) and concentrated in vacuo. Yield 6.8 g.

Workup

  1. stirringstirred for a further 24 h
  2. filtrationThe sieves were filtered
  3. washthe filtrate was washed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cad92530f2bb4c4bac0ae274992f4d4c
Source dataset
uspto-grants-2010_06
Patent number
US07737135B2

Linked notes

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