Hexane → HCID 19426938, compound

HRID 62282Notes

Reaction equation

HRID 62282 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[Li]CCCC.CCCCCC.[F:20][C:21]([F:29])([F:28])[C:22]([C:24]([F:27])([F:26])[F:25])=[O:23]>C1COCC1>[Br:8][C:4]1[N:3]=[C:2]([C:22]([OH:23])([C:24]([F:27])([F:26])[F:25])[C:21]([F:29])([F:28])[F:20])[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 122742,6-DibromopyridineHCID 12695HexafluoroacetoneHCID 178418339Butyllithium

Product 1

HCID 19426938HCID 19426938, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2,6-dibromo pyridine 260 (2.37 g, 10 mmol) in dry THF, cooled to 0° C., n-BuLi 1.4 mmol in hexane (7.9 ml, 11 mmol) was added drop wise, and stirred for 10 min. Then hexafluoroacetone (CF3—CO—CF3) 244 was added to the reaction mixture and continued stirring for another 2 h. After completion of the reaction, it was quenched with saturated ammonium chloride solution. The organic layer was separated and aqueous phase was extracted again with diethyl ether, the combined organic layer was dried over sodium sulphate and concentrated to get the crude compound 2-(6-bromopyridin-2-yl)-1,1,1,3,3,3-hexafluoropropan-2-ol 261, which was purified through 100-200 mesh silica gel by eluting the compound at 15% Ethylacetate in hexane to get the thick oil compound 261.

Workup

  1. stirringcontinued stirring for another 2 h
  2. customAfter completion of the reaction, it
  3. customwas quenched with saturated ammonium chloride solution
  4. customThe organic layer was separated
  5. extractionaqueous phase was extracted again with diethyl ether
  6. dry with materialthe combined organic layer was dried over sodium sulphate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0fcc9282264e434f90f46efff6ed0b9a
Source dataset
uspto-grants-2016_09
Patent number
US09446047B2

Reaction notes

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