1-Bromo-3,5-difluorobenzene → HCID 63331773, compound

HRID 521931Notes

Reaction equation

HRID 521931 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[CH:3]=1.[Mg].[O:11]=[C:12]1[CH2:16][CH2:15][O:14][CH2:13]1>O1CCCC1>[F:9][C:4]1[CH:3]=[C:2]([C:12]2([OH:11])[CH2:16][CH2:15][O:14][CH2:13]2)[CH:7]=[C:6]([F:8])[CH:5]=1

Participants

5

Reactant 3

HCID 1363131-Bromo-3,5-difluorobenzeneHCID 5293923-OxotetrahydrofuranHCID 5462224Magnesium

Product 1

HCID 63331773HCID 63331773, compoundYield 9.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
85 °C

Procedure

to a solution of 1-bromo-3,5-difluoro-benzene (4.00 g, 20.7 mmol) in tetrahydrofuran (70 mL) under nitrogen was added magnesium (6.0 equiv., 124 mmol) and the solution was heated at 85° C. for three hours. The solution was cooled to rt and 3-oxotetrahydrofuran (1 equiv., 20.726 mmol) in THF (20 mL) was added via syringe. The mixture was stirred at rt for three days. The reaction was quenched with sat NaHCO3, extracted with EtOAc and washed with brine. Purification by CombiFlash (0 to 100% EtOAc in heptane) provided the title compound (405 mg, 9.7%).

Workup

  1. temperatureThe solution was cooled to rt
  2. customThe reaction was quenched with sat NaHCO3
  3. extractionextracted with EtOAc
  4. washwashed with brine
  5. customPurification by CombiFlash (0 to 100% EtOAc in heptane)

Sources & evidence

ORD record
ord-423f28e73b714367a41e30e78ab25834
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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