Ethylene Glycol → 2-(4-Fluoro-3-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane

HRID 532188Notes

Reaction equation

HRID 532188 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([B:8]([OH:10])[OH:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[CH2:15](O)[CH2:16]O>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([B:8]2[O:9][CH2:16][CH2:15][O:10]2)=[CH:4][C:3]=1[C:11]([F:14])([F:12])[F:13]

Participants

4

Reactant 2

HCID 174Ethylene GlycolHCID 177500514-Fluoro-3-(trifluoromethyl)benzeneboronic acid

Product 1

HCID 866850642-(4-Fluoro-3-(trifluoromethyl)phenyl)-1,3,2-dioxaborolaneYield 115.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The mixture of 4-fluoro-3-(trifluoromethyl)phenylboronic acid (2.08 g, 10 mmol) and ethane-1,2-diol (3.72 g, 60 mmol) in toluene (150 ml) was refluxed with a Dean-stark trap for 2 h, then cooled to rt. The solvent was concentrated to dryness to afford the crude product (2.7 g, 100%). 1H NMR (300 MHz, CDCl3): δ 8.08-8.05 (d, 1H), 8.01-7.96 (t, 1H), 7.24-7.17 (t, 1H), 4.40 (s, 4H) ppm.

Workup

  1. temperaturewas refluxed with a Dean-stark trap for 2 h
  2. concentrationThe solvent was concentrated to dryness

Sources & evidence

ORD record
ord-b38ba10788334b5581ab70b3a8f48a98
Source dataset
uspto-grants-2014_10
Patent number
US08853186B2

Reaction notes

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