Hydrochloric Acid → HCID 66876242, compound

HRID 1666471Notes

Reaction equation

HRID 1666471 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([F:19])[CH:18]=1)[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][N:7]=1.[B:20](OC(C)C)([O:25]C(C)C)[O:21]C(C)C.[Li]CCCC.Cl>C1COCC1.C1(C)C=CC=CC=1>[F:19][C:17]1[CH:18]=[C:2]([B:20]([OH:25])[OH:21])[CH:3]=[C:4]([O:5][C:6]2[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][N:7]=2)[CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 668762342-(3-Bromo-5-fluorophenoxy)-5-(trifluoromethyl)-pyridineHCID 178418339Butyllithium

Product 1

HCID 66876242HCID 66876242, compoundYield 180.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

2-(3-Bromo-5-fluorophenoxy)-5-(trifluoromethyl)pyridine (2 g, 0.005 mol) and tri-isopropyl borate (1.6 mL, 0.007 mol) were dissolved in dry THF (40 mL) and toluene (10 mL) under inert atmosphere and cooled to −78° C. n-BuLi (4.48 mL, 0.005 mol) was then added dropwise at −78° C. The reaction was warmed to −20° C. and 2N HCl (2 mL) was added and then the mixture was warmed to RT. The reaction mixture was concentrated and extracted with ethyl acetate three times. The organic layer was washed with brine, dried over Na2SO4 and evaporated to dryness to give the title compound (2.71 g, 70%); m/z (300.4, M− H−).

Workup

  1. additionwas then added dropwise at −78° C
  2. temperaturethe mixture was warmed to RT
  3. concentrationThe reaction mixture was concentrated
  4. extractionextracted with ethyl acetate three times
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-36d58c324830414ea050442fe9ff4d6c
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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