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

HRID 1455732Notes

Reaction equation

HRID 1455732 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].[Li]CCCC.[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-BuLi (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, 3 H), 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-384e519af9c14837975050ac5d3f559b
Source dataset
uspto-grants-2009_01
Patent number
US07482350B2

Reaction notes

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