Hydrochloric Acid → (4-Chloro-3-methoxyphenyl)boronic acid

HRID 70556

Reaction equation

HRID 70556 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([Cl:15])[CH:8]=1.[B:16](OC)([O:19]C)[O:17]C.Cl>C1(C)C=CC=CC=1.O1CCCC1.C(OCC)(=O)C>[Cl:15][C:9]1[CH:8]=[CH:7][C:12]([B:16]([OH:19])[OH:17])=[CH:11][C:10]=1[O:13][CH3:14]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 30165374-Bromo-2-chloroanisoleHCID 178418339Butyllithium

Product 1

HCID 23005377(4-Chloro-3-methoxyphenyl)boronic acid

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

n-Butyllithium (2.76 M, 2.5 mL) was added dropwise to a solution of commercially available 4-bromo-2-chloroanisole (1.0 g) in toluene (8 mL) and tetrahydrofuran (3 mL) at −78° C., and the mixture was stirred as such for 30 minutes. Thereafter, trimethyl borate (1.0 mL) was added and the mixture was stirred at room temperature for 15 minutes. Dilute hydrochloric acid and ethyl acetate were added, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→98:2) to give the title compound as a colorless powder (535 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for 15 minutes
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→98:2)

Sources & evidence

ORD record
ord-127ee59c2c744610a05c65fd6f46695a
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Linked notes

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