Hydrochloric Acid → HCID 69065387, compound

HRID 1819498Notes

Reaction equation

HRID 1819498 reaction equation
C([C:3](CC)(CC)[CH:4](P(O)(O)=O)[C:5]([OH:7])=[O:6])C.[H-].[Na+].[Br:18][C:19]1[CH:26]=[C:25]([F:27])[C:22]([CH:23]=O)=[C:21]([F:28])[CH:20]=1.Cl.[CH2:30]1COC[CH2:31]1>>[Br:18][C:19]1[CH:26]=[C:25]([F:27])[C:22]([CH:23]=[C:4]([CH3:3])[C:5]([O:7][CH2:30][CH3:31])=[O:6])=[C:21]([F:28])[CH:20]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 27732904-Bromo-2,6-difluorobenzaldehydeHCID 57207691HCID 57207691, compound

Product 1

HCID 69065387HCID 69065387, compound

Procedure

To a THF (100 mL) solution of triethyl-2-phosphonopropionic acid (33.8 mL) was added sodium hydride (8.4 g) under ice-cooling. After the reaction mixture was stirred for 1 h, to the reaction mixture was added a THF solution of 4-bromo-2,6-difluorobenzaldehyde (2) (23.2 g) dropwise under ice-cooling. After the reaction mixture was stirred under ice-cooling for 2 h, to the reaction mixture were added ice-water, 2N hydrochloric acid, and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water, and brine, dried over magnesium sulfate, and evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate=15:1) to obtain the compoumd (3) 32.08 g.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringAfter the reaction mixture was stirred under ice-
  4. temperaturecooling for 2 h, to the reaction mixture
  5. extractionthe reaction mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with water, and brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. customThe obtained residue was purified by column chromatography (hexane:ethyl acetate=15:1)

Sources & evidence

ORD record
ord-e3ea87b3d77047d880e3dcf8ebc096d8
Source dataset
uspto-grants-2009_10
Patent number
US07601746B2

Reaction notes

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