Dimethylamine → 4-((N,N-Dimethylamino)methyl)phenylboronic acid pinacol ester

HRID 57518Notes

Reaction equation

HRID 57518 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)=[CH:5][CH:4]=1.[NH:18]([CH3:20])[CH3:19]>C1COCC1>[CH3:19][N:18]([CH3:20])[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 37345062-(4-(Bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 34604594-((N,N-Dimethylamino)methyl)phenylboronic acid pinacol ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(4-(bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (200 mg, 0.673 mmol) and aqueous Me2NH (4 mL) in THF (10 mL) was stirred at room temperature overnight. It was then concentrated under reduced pressure to give the title compound. MS (m/z): 262 (M+H)+.

Workup

  1. concentrationIt was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-acbd8a8c17224c1387a500bd99a71009
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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