Benzene, 1-iodo-2-(trifluoromethyl)- → HCID 94776684, compound

HRID 1771416Notes

Reaction equation

HRID 1771416 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([F:11])([F:10])[F:9].[Li]CCCC.[O:17]1[C@H:19]([CH2:20][CH3:21])[CH2:18]1>C1COCC1>[F:9][C:8]([F:11])([F:10])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH2:18][C@H:19]([OH:17])[CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 67957Benzene, 1-iodo-2-(trifluoromethyl)-HCID 11147670(2R)-2-EthyloxiraneHCID 178418339Butyllithium

Product 1

HCID 94776684HCID 94776684, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-Iodobenzotrifluoride (3 g) was dissolved in THF (18 ml) and was cooled to −78° C. n-BuLi (2.5 M in hexanes, 13.23 ml) was added dropwise to the reaction mixture. After 1 h, (R)-(+)-1,2-epoxybutane (1.4 ml) in THF (18 ml) was added. The reaction temperature was slowly increased to rt. The mixture was poured into ice-water (100 ml), and the product was extracted with heptane. The organic phase was washed with brine and water, dried (Na2SO4) ja evaporated under vacuum. The title compound was obtained by separation method E. (Yield 1.05 g).

Workup

  1. additionwas added dropwise to the reaction mixture
  2. extractionthe product was extracted with heptane
  3. washThe organic phase was washed with brine and water
  4. dry with materialdried (Na2SO4) ja
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-b5a09e078b65404083ccd2f657daf21b
Source dataset
uspto-grants-2016_02
Patent number
US09249127B2

Reaction notes

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