Hydrochloric Acid → 5-Chloro-2-methoxyphenylboronic acid

HRID 1532985Notes

Reaction equation

HRID 1532985 reaction equation
Br[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[O:9][CH3:10].C([Li])CCC.[B:16](OCCCC)([O:22]CCCC)[O:17]CCCC.Cl>C1COCC1.CCOCC>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([O:9][CH3:10])=[C:2]([B:16]([OH:22])[OH:17])[CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 12712Tributyl borateHCID 5219352-Bromo-4-chloroanisoleHCID 178418339Butyllithium

Product 1

HCID 27357515-Chloro-2-methoxyphenylboronic acid

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-bromo-4-chloroanisole (5.0 g, 22.6 mmol) in dry THF (60 ml) under nitrogen was cooled to −70° C. and n-butyl lithium (12.4 ml of a 2.0 M solution in hexanes, 24.8 mmol) was added. After 10 min. at −70° C. tributyl borate (8.5 ml, 31.4 mmol) was added and the temperature was allowed to rise to room temperature overnight. Aqueous hydrochloric acid (40 ml, 2 M) was added and the product was extracted with 2×60 ml ether. The ethereal phase was extracted with aqueous sodium hydroxide (2×40 ml, 1 M). Acidification with concentrated HCl during ice-cooling gave a precipitate that was dissolved in ether. Drying over magnesium sulfate and evaporation of the solvent gave the title compound. Yield 1.93 g, 46%.

Workup

  1. extractionthe product was extracted with 2×60 ml ether
  2. extractionThe ethereal phase was extracted with aqueous sodium hydroxide (2×40 ml, 1 M)
  3. temperatureAcidification with concentrated HCl during ice-cooling
  4. customgave a precipitate that
  5. dry with materialDrying over magnesium sulfate and evaporation of the solvent

Sources & evidence

ORD record
ord-8f5edac055d2482dac82517e4e20c955
Source dataset
uspto-grants-2001_03
Patent number
US06207662B1

Reaction notes

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