2-Bromoanisole → (2-Methoxyphenyl)boric acid

HRID 895618

Reaction equation

HRID 895618 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].[Mg].[B:11]([O:22]CCCC)([O:17]CCCC)[O:12]CCCC.[Cl-].[NH4+]>O1CCCC1>[CH3:9][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[O:12][B:11]([OH:22])[OH:17]

Participants

6

Reactant 4

HCID 113582-BromoanisoleHCID 12712Tributyl borateHCID 25517Ammonium ChlorideHCID 5462224Magnesium

Product 1

HCID 21940032(2-Methoxyphenyl)boric acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of 2-bromoanisole (0.25 ml) dissolved in tetrahydrofuran (5 ml) was added with magnesium (48.6 mg) and stirred at 60° C. for 1 hour to prepare a Grignard reagent. This solution was cooled to −78° C., added with a solution of tributyl borate (0.65 ml) dissolved in tetrahydrofuran (5 ml) and gradually warmed to room temperature with stirring for 20 hours. The reaction mixture was added with saturated aqueous ammonium chloride (10 ml) with ice cooling, stirred for 10 minutes and then extracted twice with ether (10 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure to obtain (2-methoxyphenyl)boric acid.

Workup

  1. temperatureThis solution was cooled to −78° C.
  2. temperaturegradually warmed to room temperature
  3. stirringwith stirring for 20 hours
  4. stirringstirred for 10 minutes
  5. extractionextracted twice with ether (10 ml)
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5fd5dc292f2c4bb09f607380a95c7a9d
Source dataset
uspto-grants-2005_07
Patent number
US06916822B2

Linked notes

Loading…