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

HRID 1852938Notes

Reaction equation

HRID 1852938 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-66a7a63a5035439d8bc2a6c4ac672750
Source dataset
uspto-grants-2015_02
Patent number
US08962619B2

Reaction notes

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