Hydrochloric Acid → HCID 86672790, compound

HRID 1755083Notes

Reaction equation

HRID 1755083 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[F:15])=[CH:9][CH:8]=1.[B:20](OC)([O:23]C)[O:21]C.Cl>O1CCCC1.C(OCC)C>[F:18][C:13]([F:19])([C:10]1[CH:11]=[CH:12][C:7]([B:20]([OH:23])[OH:21])=[CH:8][CH:9]=1)[C:14]([F:17])([F:16])[F:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 542097081-Bromo-4-(pentafluoroethyl)benzeneHCID 178418339Butyllithium

Product 1

HCID 86672790HCID 86672790, compoundYield 71.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 1.5 M solution of n-butyllithium in tetrahydrofuran (0.57 mL) was added to a solution of 1-bromo-4-pentafluoroethylbenzene (180 mg, 0.65 mmol) in diethyl ether (1.0 mL) at −78° C., and the mixture was stirred for 20 minutes. Thereafter, trimethyl borate (101 mg, 3.28 mmol) was added and the mixture was stirred at −78° C. for 10 minutes and at room temperature for 30 minutes. 6 N aqueous hydrochloric acid (200 μL) was added to the reaction mixture, and the reaction was terminated. The mixture was then purified by silica gel column chromatography to give 4-pentafluoroethylphenylboronic acid as a white solid (111 mg, 71%).

Workup

  1. stirringthe mixture was stirred at −78° C. for 10 minutes and at room temperature for 30 minutes
  2. customthe reaction was terminated
  3. customThe mixture was then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2512b2e9ae4e4e0c8a3d042b3bc0d37c
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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