Boron trifluoride etherate → HCID 20631745, compound

HRID 48008Notes

Reaction equation

HRID 48008 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([O:11][C:12]2[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14]([O:20][CH3:21])[CH:13]=2)[CH:3]=1.[BH4-].[Na+].B(F)(F)F.CCOCC>O1CCCC1>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][OH:7])=[C:4]([O:11][C:12]2[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14]([O:20][CH3:21])[CH:13]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 4311764Sodium borohydrideHCID 234318604-Bromo-2-(3,5-dimethoxyphenoxy)benzoic acid

Product 1

HCID 20631745HCID 20631745, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 75.4 g (F.W. 353.168, 213 mmol) of 4-bromo-2-(3,5-dimethoxyphenoxy)benzoic acid (22) in 300 mL of tetrahydrofuran was added 8.9 g (F.W. 37.83, 235 mmol) of sodium borohydride portionwise at room temperature and then, 31 mL (F.W. 141.93, d=1.154, 252 mmol) of boron trifluoride diethyl etherate was added thereto dropwise. The resulting solution was stirred at room temperature for one hour. To this reaction solution was added 200 mL of ice water slowly. The resulting solution was extracted with ethyl acetate and the extract was washed with a saturated sodium chloride aqueous solution three times. After drying with anhydrous magnesium sulfate, the solvent was removed under reduced pressure. The residue was recrystallized from benzene-diisopropyl ether to obtain 46.6 g (64%) of alcohol (23). (TLC; ethyl acetate:hexane=1:4).

Workup

  1. extractionThe resulting solution was extracted with ethyl acetate
  2. washthe extract was washed with a saturated sodium chloride aqueous solution three times
  3. dry with materialAfter drying with anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was recrystallized from benzene-diisopropyl ether

Sources & evidence

ORD record
ord-60847cfb0a2240859a0f188068cf3603
Source dataset
uspto-grants-2004_03
Patent number
US06700013B2

Reaction notes

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