Sodium Carbonate → HCID 67022345, compound

HRID 2198046Notes

Reaction equation

HRID 2198046 reaction equation
[F:1][C:2]1[C:8]([C:9]([F:12])([F:11])[F:10])=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].Br[CH2:14][CH:15]([OH:19])[CH2:16][CH2:17]Br.C(=O)([O-])[O-].[Na+].[Na+]>>[F:1][C:2]1[C:8]([C:9]([F:10])([F:11])[F:12])=[CH:7][CH:6]=[CH:5][C:3]=1[N:4]1[CH2:17][CH2:16][CH:15]([OH:19])[CH2:14]1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 295701,4-Dibromo-2-butanolHCID 1455693-Amino-2-fluorobenzotrifluoride

Product 1

HCID 67022345HCID 67022345, compoundYield 27.3%

Procedure

2-Fluoro-3-(trifluoromethyl)aniline (5.0 g) and 1,4-dibromobutan-2-ol (6.7 g) were stirred at 100° C. for 3 hr. After cooling to room temperature, to the reaction mixture was added saturated aqueous sodium carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate 90:10-50:50) to give the title compound (1.9 g, yield 27%) as a pale-yellow solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate 90:10-50:50)

Sources & evidence

ORD record
ord-699f03006a8d427082f6d74a85b5cd2e
Source dataset
uspto-grants-2012_12
Patent number
US08338622B2

Reaction notes

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