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

HRID 2197397Notes

Reaction equation

HRID 2197397 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 min, 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 EtOAc. 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, 3H), 2.27 (s, 3H), 2.22 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-9b67072e9bbf41a2b68b32718099f013
Source dataset
uspto-grants-2012_12
Patent number
US08338591B2

Reaction notes

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