Hydrochloric Acid → (2-Phenoxyphenyl)boronic acid

HRID 1351072Notes

Reaction equation

HRID 1351072 reaction equation
[C:1]1([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].CCC[CH2-].[B:19](OC)([O:22]C)[O:20]C.Cl>O1CCCC1>[O:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][C:6]=1[B:19]([OH:22])[OH:20])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7583Diphenyl EtherHCID 8470Trimethyl borateHCID 61028n-Butyl lithium

Product 1

HCID 2773559(2-Phenoxyphenyl)boronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Diphenyl ether (0.85 g) was dissolved in anhydrous tetrahydrofuran (20 ml) and the reaction mixture was cooled to 0° C. N-butyllithium (1.6M, 3.1 ml) was delivered by drops thereto and the reaction mixture was stirred for 30 minutes at the same temperature. Trimethyl borate (0.68 ml) was added thereto and the reaction mixture was stirred for two hours at room temperature. 1N hydrochloric acid was added to the reaction mixture and the water layer was extracted with ethyl acetate. The organic layer was dried with anhydrous sodium sulfate. The solvent was distilled off and the obtained residue was purified by column chromatography (ethyl acetate:hexane=1.5:1 to 1:3) to obtain the title compound (304 mg) having the following physical data.

Workup

  1. stirringthe reaction mixture was stirred for two hours at room temperature
  2. extractionthe water layer was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  4. distillationThe solvent was distilled off
  5. customthe obtained residue was purified by column chromatography (ethyl acetate:hexane=1.5:1 to 1:3)

Sources & evidence

ORD record
ord-fc9a122849a04f92b889fb2a05817b76
Source dataset
uspto-grants-2007_05
Patent number
US07217701B2

Reaction notes

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