Hydrochloric Acid → HCID 22989940, compound

HRID 1169515Notes

Reaction equation

HRID 1169515 reaction equation
[Mg].BrC(Br)C.Br[C:7]1[CH:8]=[C:9]([CH3:20])[C:10]([O:14][CH2:15][CH2:16][O:17][CH2:18][CH3:19])=[C:11]([CH3:13])[CH:12]=1.[B:21]([O:26]C)([O:24]C)[O:22]C.Cl>C1COCC1>[CH2:18]([O:17][CH2:16][CH2:15][O:14][C:10]1[C:9]([CH3:20])=[CH:8][C:7]([O:22][B:21]([OH:26])[OH:24])=[CH:12][C:11]=1[CH3:13])[CH3:19]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 112011,1-DibromoethaneHCID 5462224MagnesiumHCID 22990124HCID 22990124, compound

Product 1

HCID 22989940HCID 22989940, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
55 °C

Procedure

A suspension of magnesium (2.36 g) in THF (100 ml) was stirred under a nitrogen atmosphere, and thereto was added dibromoethane (a catalytic amount) and was subsequently added dropwise a solution of 5-bromo-2-(2-ethoxyethoxy)-1,3-dimethylbenzene (24.1 g) in anhydrous THF (100 ml). The resulting mixture was heated at 55° C. for 2.5 hours and was then cooled to −78° C., and thereto was added dropwise trimethyl borate (19.8 ml). The reaction mixture was brought back to the room temperature and was stirred overnight. The reaction mixture was mixed with 1 N hydrochloric acid, was concentrated and was extracted with ethyl acetate. The organic layer was washed with water and an aqueous saturated solution of sodium chloride, and was dried with anhydrous magnesium sulfate. The resulting organic layer was evaporated under reduced pressure to remove the solvent to obtain 4-(2-ethoxyethoxy)-3,5-dimethylphenylboric acid (8.4 g) as colorless crystals.

Workup

  1. temperaturewas then cooled to −78° C.
  2. customwas brought back to the room temperature
  3. stirringwas stirred overnight
  4. concentrationwas concentrated
  5. extractionwas extracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materialan aqueous saturated solution of sodium chloride, and was dried with anhydrous magnesium sulfate
  8. customThe resulting organic layer was evaporated under reduced pressure
  9. customto remove the solvent

Sources & evidence

ORD record
ord-094b26cd8aec408bb2450cd941e96563
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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