Acetone → HCID 58335251, compound

HRID 2060621Notes

Reaction equation

HRID 2060621 reaction equation
Br[C:2]1[CH:3]=[C:4]([F:16])[C:5]([CH:9]([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])=[C:6]([F:8])[CH:7]=1.[Li]CCCC.[CH3:22][C:23]([CH3:25])=[O:24]>C(OC)(C)(C)C>[CH2:11]([O:10][CH:9]([O:13][CH2:14][CH3:15])[C:5]1[C:4]([F:16])=[CH:3][C:2]([C:23]([OH:24])([CH3:25])[CH3:22])=[CH:7][C:6]=1[F:8])[CH3:12]

Participants

5

Reactant 3

HCID 180AcetoneHCID 58335267HCID 58335267, compoundHCID 178418339Butyllithium

Product 1

HCID 58335251HCID 58335251, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 5-bromo-2-(diethoxymethyl)-1,3-difluorobenzene (14.7 g, 0.05 mol) in t-butylmethylether (290 mL) was added n-BuLi (21 mL of 2.5 M in hexanes, 0.052 mol) at −78° C. under argon. The reaction was then stirred at −78° C. for 1 hour. Acetone (4.9 mL, 0.065 mol) was added dropwise to the reaction mixture. The reaction solution was then slowly warmed to 0° C. and stirred for 30 min. The reaction was quenched with saturated aqueous sodium bicarbonate. The mixture was extracted with ethyl acetate. The organic phase was dried and concentrated to afford the title compound. No further purification was performed. 1H NMR (300 MHz, CDCl3): δ 10.34 (s, 1H), 87.03 (d, 2H), 5.74 (s, 1H), 3.85-3.71 (m, 2H), 3.60 (q, 2H), 1.52 (s, 6H), 1.24 (t, 6H).

Workup

  1. temperatureThe reaction solution was then slowly warmed to 0° C.
  2. stirringstirred for 30 min
  3. customThe reaction was quenched with saturated aqueous sodium bicarbonate
  4. extractionThe mixture was extracted with ethyl acetate
  5. customThe organic phase was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-475f13210ef14b09ac775a014639a2af
Source dataset
uspto-grants-2012_10
Patent number
US08278335B2

Reaction notes

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