Ethyl Bromide → N,N-Diethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

HRID 57525

Reaction equation

[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[O:3]1.Br[CH2:18][CH3:19].[H-].[Na+].[CH2:22]1COC[CH2:23]1>>[CH2:22]([N:15]([CH2:18][CH3:19])[C:12]1[CH:13]=[CH:14][C:9]([B:4]2[O:3][C:2]([CH3:16])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]2)=[CH:10][CH:11]=1)[CH3:23]

Participants

Reactant 4

HCID 6332Ethyl Bromide

HCID 8028Tetrahydrofuran

HCID 24758Sodium hydride

HCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 44629855N,N-Diethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Procedure

A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine (100 mg, 0.45 mmol) and bromoethane (200 mg, 1.8 mmol), NaH (100 mg, 1.8 mmol) in THF was stirred at room temperature overnight, and concentrated in vacuo to give the crude title compound used for the next step. MS (m/z): 276 (M+H)+.

Workup

concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-d87bad50eb66433bb162f6a1119d5ebd
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434726B2

Linked notes

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