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

HRID 1840681Notes

Reaction equation

HRID 1840681 reaction equation
[OH:1][C:2]([C:5]([OH:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14](Br)=[CH:13][C:12]=1[OH:18].CCN(CC)CC.[B:26]([O-])([O-])[O-]>O1CCOCC1>[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([B:26]2[O:8][C:5]([CH3:7])([CH3:6])[C:2]([CH3:4])([CH3:3])[O:1]2)=[CH:13][C:12]=1[OH:18]

Participants

6

Reactant 4

HCID 6425PinacolHCID 8471TriethylamineHCID 26574BorateHCID 1422285-Bromo-2-methoxyphenol

Product 1

HCID 177502512-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent4×

Procedure

A solution of pinacol (11.29 g; 0.0955 mol) in dry dioxane (40 ml) was added dropwise, over an hour, to a solution of borane-methyl sulphide complex (9.0 ml; 10M; 0.090 mol) in dioxane (40 ml) and stirred at RT under N2. To this solution was added HB(pin) (22.0 ml; 0.152 mol) and 2-methoxy-5-bromophenol (19.63 g; 0.0967 mol) in dioxane (30 ml). This solution was allowed to stir overnight at room temperature before being added, dropwise, to the activated catalyst [PdCl2(dppf)CH2Cl2 (2.38 g; 2.91 mmol) and NEt3 (40.0 ml; 0.287 mol) in dry dioxane (450 ml) heated at 80° C. and allowed to cool to RT]. The reaction mixture was heated at 100° C. GC analysis after 18 hours showed the desired borate compound at 12.0 minutes.

Workup

  1. stirringto stir overnight at room temperature
  2. additionbefore being added
  3. temperatureThe reaction mixture was heated at 100° C

Sources & evidence

ORD record
ord-25e87337908a41eb9141bd9b581d5df2
Source dataset
uspto-grants-2004_01
Patent number
US06680401B1

Reaction notes

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