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

HRID 1853917Notes

Reaction equation

HRID 1853917 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([B:12]([OH:14])[OH:13])=[CH:8][CH:7]=1.O[C:16]([C:19](O)([CH3:21])[CH3:20])([CH3:18])[CH3:17]>C(OCC)C>[Br:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([B:12]2[O:14][C:19]([CH3:21])([CH3:20])[C:16]([CH3:18])([CH3:17])[O:13]2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 6425PinacolHCID 44119698[4-(3-Bromopropoxy)phenyl]boronic acid

Product 1

HCID 441197642-[4-(3-Bromopropoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneYield 112.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 4-(3-bromopropoxy)phenylboronic acid (1.0 g, 3.9 mmol) in diethyl ether (40 mL) was added pinacol (1.4 g, 12 mmol) and the reaction mixture was stirred for 18 h and concentrated to afford the desired product (1.5 g, crude) as a light brown oil which carried onto the next step without further purification: ESI MS m/z 247 [C15H22BBrO3−94]+.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-d23cd9f2f01b4a01a19fe36250da671f
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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