Triethylamine → 2-Fluoro-5-((3-oxo-4,5,6,7-tetrahydroisobenzofuran-1 (3h)-ylidene)methyl)benzonitrile

HRID 925062Notes

Reaction equation

HRID 925062 reaction equation
[Br-].C([P+](CCCC)(CCCC)[CH:7]1[C:11]2[CH2:12][CH2:13][CH2:14][CH2:15][C:10]=2[C:9](=[O:16])[O:8]1)CCC.[F:25][C:26]1[CH:33]=[CH:32][C:31]([CH:34]=O)=[CH:30][C:27]=1[C:28]#[N:29].C(N(CC)CC)C>ClCCl>[F:25][C:26]1[CH:33]=[CH:32][C:31]([CH:34]=[C:7]2[C:11]3[CH2:12][CH2:13][CH2:14][CH2:15][C:10]=3[C:9](=[O:16])[O:8]2)=[CH:30][C:27]=1[C:28]#[N:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27695822-Fluoro-5-formylbenzonitrileHCID 66966753Tributyl(3-oxo-1,3,4,5,6,7-hexahydro-2-benzofuran-1-yl)phosphonium bromide

Product 1

HCID 690434422-Fluoro-5-((3-oxo-4,5,6,7-tetrahydroisobenzofuran-1 (3h)-ylidene)methyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of EXAMPLE 1B (3.05 g) in dichloromethane (30 mL) was added 2-fluoro-5-formylbenzonitrile (1.08 g) and triethylamine (1.02 mL). The mixture was stirred at ambient temperature for 16 hours and concentrated. The concentrate was partitioned between ethyl acetate and brine. The organic layer was washed with brine and concentrated. The concentrate was purified by flash chromatography on silica gel with 50% ethyl acetate in hexane.

Workup

  1. concentrationconcentrated
  2. customThe concentrate was partitioned between ethyl acetate and brine
  3. washThe organic layer was washed with brine
  4. concentrationconcentrated
  5. customThe concentrate was purified by flash chromatography on silica gel with 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-080e7bc1d94a4ed0964a2514e15399a9
Source dataset
uspto-grants-2016_03
Patent number
US09283222B2

Reaction notes

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