Boron trifluoride etherate → HCID 71743722, compound

HRID 2277634Notes

Reaction equation

HRID 2277634 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[C:4]#[N:5].[CH3:11][CH2:12][Mg+].[Br-].B(F)(F)F.CCOCC>C1COCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[C:4]1([NH2:5])[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 103309442-Bromo-5-chlorobenzonitrileHCID 178461630HCID 178461630, compound

Product 1

HCID 71743722HCID 71743722, compoundYield 17.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-bromo-5-chlorobenzonitrile (10 g, 46 mmol) and Ti(Oi-Pr)4 (16.64 mL, 55 mmol) in THF (200 mL) at −78° C. was added EtMgBr (138 mL, 138 mmol) dropwise. The reaction mixture was allowed to warm up to room temperature and stirred for 2 hours. BF3-Et2O (17.2 mL) was added, and the solution was stirred for another 16 hours before it was quenched with aq. HCl solution and washed with EtOAc. The aqueous phase was adjusted to pH˜10 with aq. NaOH solution, and exacted with EtOAc (3×). The combined organic layers were concentrated to give a crude product which was purified by chromatography to afford title compound (2 g, yield 17.6%). MS: 246.7 (M+H+, 1C1) as oil.

Workup

  1. stirringthe solution was stirred for another 16 hours before it
  2. customwas quenched with aq. HCl solution
  3. washwashed with EtOAc
  4. concentrationThe combined organic layers were concentrated
  5. customto give a crude product which
  6. customwas purified by chromatography

Sources & evidence

ORD record
ord-4d1c1e48f3d64b2d84f15e6f0d85ab15
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

Loading…