Triethylamine → 2-Fluoro-5-((3-oxoisobenzofuran-1(3H)-ylidene)methyl)benzonitrile

HRID 1466737Notes

Reaction equation

HRID 1466737 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([CH:10]=O)=[CH:6][C:3]=1[C:4]#[N:5].[O:12]=[C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15](P(=O)(OC)OC)[O:14]1.C(N(CC)CC)C>C1COCC1>[F:1][C:2]1[CH:9]=[CH:8][C:7]([CH:10]=[C:15]2[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:13](=[O:12])[O:14]2)=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27695822-Fluoro-5-formylbenzonitrileHCID 11118213Dimethyl (3-oxo-1,3-dihydro-2-benzofuran-1-yl)phosphonate

Product 1

HCID 671224512-Fluoro-5-((3-oxoisobenzofuran-1(3H)-ylidene)methyl)benzonitrileYield 92.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 2-fluoro-5-formylbenzonitrile (0.74 g, 5 mmol) and dimethyl 3-oxo-1,3-dihydroisobenzofuran-1-ylphosphonate (1.2 g, 5 mmol) in THF (30 ml) was added triethylamine (0.7 ml, 5 mmol) dropwise at a temperature of below 15° C., which was then slowly rose to ambient temperature and stirred for overnight. The reaction mixture was concentrated and the residue was added water and stirred for 30 min. The precipitated solid was collected by filtration, washed with water, hexane, and ether, and dried in vacuo to afford the target compound (1.2 g, 92.3%) as a light yellow solid (a 50:50 mixture of E and Z isomers), used in next step without further purification.

Workup

  1. customwas then slowly rose to ambient temperature
  2. concentrationThe reaction mixture was concentrated
  3. additionthe residue was added water
  4. stirringstirred for 30 min
  5. filtrationThe precipitated solid was collected by filtration
  6. washwashed with water, hexane, and ether
  7. customdried in vacuo

Sources & evidence

ORD record
ord-0a2f8ab8295644a5a23a1cd1d90a030b
Source dataset
uspto-grants-2015_04
Patent number
US08999985B2

Reaction notes

Loading…