2-Bromoethanol → 2-{[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]amino}ethanol

HRID 1914047Notes

Reaction equation

HRID 1914047 reaction equation
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=2)[NH2:12])[O:3]1.Br[CH2:18][CH2:19][OH:20].C(N(CC)C(C)C)(C)C>C1(C)C=CC=CC=1>[CH3:8][C:6]1([CH3:7])[C:2]([CH3:16])([CH3:1])[O:3][B:4]([C:9]2[CH:10]=[C:11]([NH:12][CH2:18][CH2:19][OH:20])[CH:13]=[CH:14][CH:15]=2)[O:5]1

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 81531DiisopropylethylamineHCID 27346553-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 711385082-{[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]amino}ethanolYield 29%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (219 mg, 1.00 mmol), 2-bromoethanol (82.7 μL, 1.10 mmol) and N,N-diisopropylethylamine (261 μL, 1.50 mmol) in toluene (2 mL) was refluxed for 22 hours. After cooling to room temperature, the mixture was concentrated. The residue was purified by silica gel column chromatography (EtOAc/hexane=2:1→1:1) to afford desired product (76.3 mg, 29.0%) as colorless oil.

Workup

  1. temperaturewas refluxed for 22 hours
  2. concentrationthe mixture was concentrated
  3. customThe residue was purified by silica gel column chromatography (EtOAc/hexane=2:1→1:1)

Sources & evidence

ORD record
ord-9b4f1c79e4694aeb8418bd6ed164796d
Source dataset
uspto-grants-2013_12
Patent number
US08609688B2

Reaction notes

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