Boron trifluoride etherate → HCID 20258830, compound

HRID 730077Notes

Reaction equation

HRID 730077 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.B(F)(F)F.CCOCC.[OH-].[Na+]>ClCCl>[Br:1][C:2]1[C:3]2[O:4][C:5]3[C:6](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:7](=[O:9])[C:14]=2[CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 9845Trifluoroacetic anhydrideHCID 14798Sodium HydroxideHCID 28604678HCID 28604678, compound

Product 1

HCID 20258830HCID 20258830, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2-bromophenoxy)-benzoic acid 2j (11.8 g, 40.3 mmol) in dichloromethane (200 mL) was added trifluoroacetic anhydride (6.3 mL, 44.6 mmol), and the mixture was stirred for 30 min at rt. Boron trifluoride etherate (0.51 mL, 4.03 mmol) was added, and the mixture was stirred for 2 h at rt. The mixture was cooled in an ice bath, and a 3N sodium hydroxide solution (100 mL) was added under vigorous stirring. The organic layer was separated, washed with water and brine, dired over magnesium sulfate, filtered, and evaporated. The residue was purified over silica gel using dichloromethane as eluent. The desired fractions were collected, and evaporated to yield 10.18 g (91.8%) of title compound 3j.

Workup

  1. stirringthe mixture was stirred for 2 h at rt
  2. temperatureThe mixture was cooled in an ice bath
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified over silica gel
  8. customThe desired fractions were collected
  9. customevaporated

Sources & evidence

ORD record
ord-1054cbbaeda54899a1f653077cfc292a
Source dataset
uspto-grants-2009_09
Patent number
US07582650B2

Reaction notes

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