Hydrochloric Acid → 2-Methoxyphenylboronic acid

HRID 1419566Notes

Reaction equation

HRID 1419566 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14].C[O:16][B:17](OC)[O:18]C.Cl>O1CCCC1>[CH3:14][O:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[B:17]([OH:18])[OH:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 113582-BromoanisoleHCID 178418339Butyllithium

Product 1

HCID 27339582-Methoxyphenylboronic acidYield 105.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

n-Butyllithium (1.6M in hexane, 13.0 mL) was added to a stirred, cooled (-78° C.) solution of 2-bromoanisole (3.74 g) in tetrahydrofuran (20 mL) and the mixture was stirred at -78° C. for 20 min. Trimethylborate (5.92 g) was added and the solution was allowed to warm to room temperature and stirred for 24 h. The mixture was cooled to 0° C. and acidified with aqueous hydrochloric acid (5M). The mixture was extracted with dichloromethane (4×50 mL) and the combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound as a colorless solid (3.2 g), δH (CDCl3) 3.91 (3H, s), 6.09 (2H, s), and 6.87-7.03 (4H, m).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 24 h
  3. temperatureThe mixture was cooled to 0° C.
  4. extractionThe mixture was extracted with dichloromethane (4×50 mL)
  5. dry with materialthe combined organic fractions were dried (MgSO4)
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-3562fa6f2c8d4aefaecadbbfe3910291
Source dataset
uspto-grants-1999_03
Patent number
US05885999

Reaction notes

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