Water → HCID 58762224, compound

HRID 858753Notes

Reaction equation

HRID 858753 reaction equation
[CH:1]1([CH:6]([OH:9])[CH:7]=[CH2:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[F:10][C:11]1[CH:16]=[C:15](Br)[CH:14]=[CH:13][C:12]=1[CH:18]([F:20])[F:19].C([O-])(O)=O.[Na+].O>CN1C(=O)CCC1>[CH:1]1([C:6](=[O:9])[CH2:7][CH2:8][C:15]2[CH:14]=[CH:13][C:12]([CH:18]([F:20])[F:19])=[C:11]([F:10])[CH:16]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 1451331-Cyclopentyl-2-propen-1-olHCID 516892Sodium BicarbonateHCID 27611824-Bromo-1-(difluoromethyl)-2-fluorobenzene

Product 1

HCID 58762224HCID 58762224, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 1-cyclopentyl-2-propen-1-ol (34 g, 0.266 mol), 2-fluoro-4-bromo-difluoromethyl benzene, (40 g, 0.177 mol, 1.5 equiv), and NaHCO3 (17.8 g, 0.212 mol, 1.2 equiv) in anhydrous NMP (200 mL) was heated to 140° C. for 1 h, resulting in complete conversion by TLC. The reaction mixture was poured into water and extracted with CH2Cl2. The organic layer was separated, washed with brine and dried over anhydrous Na2SO4. After the removal of the solvent, the residue was purified by column chromatography using hexanes/ethyl acetate, and the product-containing fractions combined and concentrated. The residue was fractionally distilled through a Vigreux column to give 16 g (33%) of the desired product (bp 100° C./0.2 Torr).

Workup

  1. customresulting in complete conversion by TLC
  2. extractionextracted with CH2Cl2
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customAfter the removal of the solvent
  7. customthe residue was purified by column chromatography
  8. concentrationconcentrated
  9. distillationThe residue was fractionally distilled through a Vigreux column

Sources & evidence

ORD record
ord-b4d40d88b5354359b1551bf8c17d591d
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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