Pinacol → 4-Carboxy-3-fluorobenzeneboronic acid pinacol ester

HRID 1867855Notes

Reaction equation

HRID 1867855 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([B:11]([OH:13])[OH:12])[CH:5]=[CH:6][C:7]=1[C:8]([OH:10])=[O:9].O[C:15]([C:18](O)([CH3:20])[CH3:19])([CH3:17])[CH3:16]>C1(C)C=CC=CC=1.CCO>[F:1][C:2]1[CH:3]=[C:4]([B:11]2[O:13][C:18]([CH3:20])([CH3:19])[C:15]([CH3:17])([CH3:16])[O:12]2)[CH:5]=[CH:6][C:7]=1[C:8]([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 6425PinacolHCID 27632014-Carboxy-3-fluorophenylboronic acid

Product 1

HCID 447176654-Carboxy-3-fluorobenzeneboronic acid pinacol ester

Reagents, catalysts & solvents 1

HCID 21863594Toluene ethanolSolvent

Procedure

3-Fluoro-4-carboxy-phenylboronic acid (CAS 120153-08-4)(1.0 g, 5.4 mmol) and pinacol (0.645 g, 5.4 mmol) were stirred in Toluene/EtOH (1:1) (30 ml) with heating to give a thick white slurry. The mixture was concentrated under reduced pressure, toluene (30 ml) was added and the mixture was again concentrated under reduced pressure to a white solid. LCMS(-ve ion mode) showed a single peak trace with 265 (M−H RP). The material was dried under high vacuum overnight to give 1.42 g.

Workup

  1. temperaturewith heating
  2. customto give a thick white slurry
  3. concentrationThe mixture was concentrated under reduced pressure, toluene (30 ml)
  4. additionwas added
  5. concentrationthe mixture was again concentrated under reduced pressure to a white solid
  6. customThe material was dried under high vacuum overnight
  7. customto give 1.42 g

Sources & evidence

ORD record
ord-94e43b51c2a64857841454975dfbbd47
Source dataset
uspto-grants-2009_12
Patent number
US07632857B2

Reaction notes

Loading…