Triethylamine → Phenylboronic acid pinacol ester

HRID 1244885Notes

Reaction equation

HRID 1244885 reaction equation
C(N([CH2:6][CH3:7])CC)C.FC(F)(F)S(O[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=O)=O.[C:22]1([O:28][B:29]([O-])[O-:30])[CH:27]=CC=C[CH:23]=1.O1CCOC[CH2:33]1>>[CH3:33][C:6]1([CH3:7])[C:22]([CH3:27])([CH3:23])[O:28][B:29]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:30]1

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 312751,4-Dioxane2×HCID 548641Phenyl TrifluoromethanesulfonateHCID 19793864Phenylborate

Product 1

HCID 570673Phenylboronic acid pinacol ester

Conditions

Temperature
80 °C

Procedure

In a reaction tube under nitrogen, a mixture of PdCl2(dppf)CH2Cl2 (23 mg; 0.028 mmol) and triethylamine (0.36 ml; 2.58 mmol) in dioxane (4 ml; dried over 4 Å sieves) was sealed and stirred at 80° C. overnight (18 h). After cooling to room temperature, 1.29M HB(pin) in dioxane (1.00 ml; 1.29 mmol) and phenyl trifluoromethanesulfonate (197 mg; 0.871 mmol) were added and the reaction mixture was stirred at 80° C. GC analysis after 4 days showed a new peak at 7.4 minutes which was identified by GC/MS as the desired phenylborate compound.

Workup

  1. customwas sealed
  2. temperatureAfter cooling to room temperature
  3. stirringthe reaction mixture was stirred at 80° C
  4. waitGC analysis after 4 days showed

Sources & evidence

ORD record
ord-95b5015a277441deb8b9b0428ff19a15
Source dataset
uspto-grants-2006_10
Patent number
US07122694B2

Reaction notes

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