HCID 68682176, compound → HCID 57951098, compound

HRID 1171080Notes

Reaction equation

HRID 1171080 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2([CH2:14][CH3:15])OCC[O:10]2)=[CH:4][C:3]=1[F:16]>Cl.O1CCCC1.C(O)(=O)C.C(OCC)(=O)C>[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9](=[O:10])[CH2:14][CH3:15])=[CH:4][C:3]=1[F:16]

Participants

4

Reactant 1

HCID 68682176HCID 68682176, compound

Product 1

HCID 57951098HCID 57951098, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 67832163HCID 67832163, compoundSolvent

Procedure

2-(4-Bromo-3,5-difluorophenyl)-2-ethyl-1,3-dioxolane (1.20 g) was dissolved in 1 N hydrochloric acid/tetrahydrofuran/acetic acid (1/1/1, 30 ml). The reaction liquid was stirred overnight with heating under reflux, then diluted with ethyl acetate, and washed with aqueous saturated sodium hydrogencarbonate solution. The organic layer was dried with anhydrous sodium sulfate, then the solvent was evaporated off, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1) to obtain the entitled compound (806 mg) as a pale yellow oil.

Workup

  1. customThe reaction liquid
  2. temperaturewith heating
  3. temperatureunder reflux
  4. washwashed with aqueous saturated sodium hydrogencarbonate solution
  5. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  6. customthe solvent was evaporated off
  7. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-aae71a0fc33f4820aae6787d99fa7edc
Source dataset
uspto-grants-2010_11
Patent number
US07829586B2

Reaction notes

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