Hydrochloric Acid → HCID 22990125, compound

HRID 1169511Notes

Reaction equation

HRID 1169511 reaction equation
[Mg].BrC(Br)C.Br[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][O:16][CH2:17][CH3:18])=[CH:9][CH:8]=1.[B:19]([O:24]C)([O:22]C)[O:20]C.Cl>C1COCC1>[CH2:17]([O:16][CH2:15][CH2:14][CH2:13][C:10]1[CH:11]=[CH:12][C:7]([O:20][B:19]([OH:24])[OH:22])=[CH:8][CH:9]=1)[CH3:18]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 112011,1-DibromoethaneHCID 5462224MagnesiumHCID 22990070HCID 22990070, compound

Product 1

HCID 22990125HCID 22990125, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

A suspension of magnesium (0.37 g) in THF (5 ml) was stirred under a nitrogen atmosphere, and thereto was then added dibromoethane (a catalytic amount) and was subsequently added dropwise a solution of 1-bromo-4-(3-ethoxypropyl)benzene (3.4 g) in anhydrous THF (30 ml). The resulting mixture was heated at 50° C. for 1.5 hours and was then cooled to −78° C., and thereto was added dropwise trimethyl borate (3.1 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, and the residue was purified by silica gel chromatography (ethyl acetate/triethylamine) to obtain 4-(3-ethoxypropyl)phenylboric acid (1.25 g) as a light yellow, oily substance.

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
  10. customthe residue was purified by silica gel chromatography (ethyl acetate/triethylamine)

Sources & evidence

ORD record
ord-79034ac61e4f4267b8a1211b04c5d172
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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