Carbon Dioxide → HCID 22314472, compound

HRID 966093Notes

Reaction equation

HRID 966093 reaction equation
[Li]CCCC.[F:6][C:7]1[CH:8]=[C:9]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH:10]=[C:11]([F:13])[CH:12]=1.[C:23](=[O:25])=[O:24]>C1COCC1>[F:6][C:7]1[CH:8]=[C:9]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH:10]=[C:11]([F:13])[C:12]=1[C:23]([OH:25])=[O:24]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 22314510HCID 22314510, compoundHCID 178418339Butyllithium

Product 1

HCID 22314472HCID 22314472, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

BuLi (1.6 M in hexane, 27.1 mL, 43.4 mmol) was added to a solution of 3,5-difluoro-(4-fluoro-benzyloxy)-benzene (10.5 g, 41.4 mmol) in dry THF at −78° C., under Argon, and the reaction mixture maintained at this temperature for 1 h whereupon carbon dioxide gas was bubbled into the solution over a 10 min period. The reaction mixture was then warmed up to room temperature and water added. The resulting mixture was extracted with diethyl ether. The aqueous phase was adjusted to pH 2 with HCl and extracted with ethyl acetate. The combined ethyl acetate layers were washed with HCl (0.1 N), then dried over sodium sulfate, filtered and evaporated to leave a white solid. This was triturated with pentane-diethyl ether to afford the title compound (6.8 g, 59%) as a white solid. MS: m/e=280.9 (M−H−).

Workup

  1. customwas bubbled into the solution over a 10 min period
  2. additionwater added
  3. extractionThe resulting mixture was extracted with diethyl ether
  4. extractionextracted with ethyl acetate
  5. washThe combined ethyl acetate layers were washed with HCl (0.1 N)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customto leave a white solid
  10. customThis was triturated with pentane-diethyl ether

Sources & evidence

ORD record
ord-64cd776993944e198acc7bd8f3e9e123
Source dataset
uspto-grants-2005_10
Patent number
US06951884B2

Reaction notes

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