Hydrochloric Acid → (3-Methoxy-2,6-dimethylphenyl)boronic acid

HRID 1392601Notes

Reaction equation

HRID 1392601 reaction equation
[CH3:1][C:2]1[C:7](Br)=[C:6]([CH3:9])[CH:5]=[CH:4][C:3]=1[O:10][CH3:11].C([Li])CCC.[B:17](OC)([O:20]C)[O:18]C.Cl>C1COCC1>[CH3:1][C:2]1[C:3]([O:10][CH3:11])=[CH:4][CH:5]=[C:6]([CH3:9])[C:7]=1[B:17]([OH:20])[OH:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 126177352-Bromo-4-methoxy-1,3-dimethylbenzeneHCID 178418339Butyllithium

Product 1

HCID 45091285(3-Methoxy-2,6-dimethylphenyl)boronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2,4-dimethyl-3-bromoanisole (3.3 g, 15 mmol) in THF (15 mL) is added dropwise at −78° C. to a solution of n-butyllithium (11 mL of 1.6M in hexane, 17 mmol) in THF (35 mL). After 30 minutes, trimethyl borate (2.3 mL, 20 mmol) is added and the mixture is allowed to warm to room temperature overnight. The mixture is poured onto 10% HCl and extracted with ethyl acetate. The organic fraction is washed with saturated brine, dried (Na2SO4), and concentrated to give the desired product as a brownish oil. 1H NMR (CDCl3) 6.98 (d, 1H), 6.75 (d, 1H), 4.64 (br s), 3.80 (s, 3 H), 2.27 (s, 3H), 2.22 (s, 3H)

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic fraction is washed with saturated brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fabc01d648864b76aa26aadefba1c08d
Source dataset
uspto-grants-2008_03
Patent number
US07342115B2

Reaction notes

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