Boron trifluoride etherate → HCID 67281057, compound

HRID 1694725Notes

Reaction equation

HRID 1694725 reaction equation
B(F)(F)F.CCOCC.[F:10][C:11]([F:30])([F:29])[C:12]1[CH:28]=[CH:27][C:15]([O:16][CH2:17][C:18]([O:20][CH2:21][C:22]2([CH3:26])[CH2:25][O:24][CH2:23]2)=[O:19])=[CH:14][CH:13]=1>ClCCl>[CH3:23][C:22]12[CH2:25][O:24][C:18]([CH2:17][O:16][C:15]3[CH:27]=[CH:28][C:12]([C:11]([F:30])([F:29])[F:10])=[CH:13][CH:14]=3)([O:19][CH2:26]1)[O:20][CH2:21]2

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 86609219[4-(Trifluoromethyl)phenoxy]-acetic acid, (3-methyl-3-oxetanyl)methyl ester

Product 1

HCID 67281057HCID 67281057, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron trifluoride diethyl etherate (1.48 ml) was added to a solution of the product from step (ii) (14.2 g) in dichloromethane at −78° C. The cooling bath was removed, the mixture, stirred for 3 h then triethylamine (6.2 ml) added. The mixture was reduced to half the volume under reduced pressure then filtered. The filtrate was evaporated under reduced pressure then the residue purified by chromatography on silica (pre-eluted with one column volume of neat triethylamine) eluting with dichloromethane, yield 11.1 g.

Workup

  1. customThe cooling bath was removed
  2. additiontriethylamine (6.2 ml) added
  3. filtrationthen filtered
  4. customThe filtrate was evaporated under reduced pressure
  5. customthe residue purified by chromatography on silica (pre-eluted with one column volume of neat triethylamine)
  6. washeluting with dichloromethane, yield 11.1 g

Sources & evidence

ORD record
ord-8874e256ae6c4f94aecef261fbcafe04
Source dataset
uspto-grants-2012_04
Patent number
US08158820B2

Reaction notes

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