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

HRID 886983Notes

Reaction equation

HRID 886983 reaction equation
COP([CH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[O:8]1)(=O)OC.C(N(CC)CC)C.[F:24][C:25]1[CH:32]=[CH:31][C:30]([CH:33]=O)=[CH:29][C:26]=1[C:27]#[N:28]>O1CCCC1>[F:24][C:25]1[CH:32]=[CH:31][C:30]([CH:33]=[C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:16])[O:8]2)=[CH:29][C:26]=1[C:27]#[N:28]

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 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

To a mixture of (3-oxo-1,3-dihydro-isobenzofuran-1-yl)phosphonic acid dimethyl ester (G) in tetrahydrofuran and 2-fluoro-5-formylbenzonitrile (F) in tetrahydrofuran was added triethylamine drop-wise over 25 min, with the temperature kept below 15° C. The reaction mixture was warmed slowly to 20° C. over 1 hour and concentrated in vacuo. The white residue was slurried in water or 30 minutes, filtered, washed with water, hexane and ether, and dried to yield 2-fluoro-5-(3-oxo-3H-isobenzofuran-1-ylidenemethyl)benzonitrile (E) as a 50:50 mixture of E and Z isomers (yield: 96%).

Workup

  1. customkept below 15° C
  2. concentrationconcentrated in vacuo
  3. filtrationfiltered
  4. washwashed with water, hexane and ether
  5. customdried

Sources & evidence

ORD record
ord-7b324b823f57412ebd1b7ab0d322f379
Source dataset
uspto-grants-2012_08
Patent number
US08247416B2

Reaction notes

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