Dichloromethane → HCID 67044484, compound

HRID 2261972Notes

Reaction equation

HRID 2261972 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[C:18]([F:19])=[CH:17][CH:16]=[C:15]([F:20])[C:11]=2[C:12]([OH:14])=[O:13])=O)=[CH:4][C:3]=1[N+:21]([O-:23])=[O:22].ClCCl.N1C(F)=NC(F)=NC=1[F:29]>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([F:29])[C:10]3[C:18]([F:19])=[CH:17][CH:16]=[C:15]([F:20])[C:11]=3[C:12](=[O:14])[O:13]2)=[CH:4][C:3]=1[N+:21]([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 12664Cyanuric fluorideHCID 67044866HCID 67044866, compound

Product 1

HCID 67044484HCID 67044484, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-[(4-chloro-3-nitrophenyl)carbonyl]-3,6-difluorobenzoic acid (7.0 g, 22.00 mmol) at 0° C. in anhydrous dichloromethane (40 mL) pyridine (1.70 ml, 22.00 mmol) was added, followed by the addition of cyanuric fluoride (1.90 ml, 24.20 mmol). The reaction mixture was stirred for 120 minutes at 0° C. Water (35 mL) was added to the reaction mixture and it was stirred for 10 min at 0° C. The resulting slurry was filtered through a pad of Celite and washed with dichloromethane. The filtrate was partitioned with water and the organic layer was washed with water. It was dried over anhydrous sodium sulfate. Filtration and concentration gave a crystalline product. It was collected by filtration and dried in vacuo, to give 3-(4-chloro-3-nitrophenyl)-3,4,7-trifluoro-2-benzofuran-1(3H)-one (5.77 g, 82% yield). MS (EI) for C14H5ClF3NO4: 342 (M−).

Workup

  1. stirringwas stirred for 10 min at 0° C
  2. filtrationThe resulting slurry was filtered through a pad of Celite
  3. washwashed with dichloromethane
  4. customThe filtrate was partitioned with water
  5. washthe organic layer was washed with water
  6. dry with materialIt was dried over anhydrous sodium sulfate
  7. filtrationFiltration and concentration
  8. customgave a crystalline product
  9. filtrationIt was collected by filtration
  10. customdried in vacuo

Sources & evidence

ORD record
ord-7adac29620a04333b5047681d7b4e5a6
Source dataset
uspto-grants-2010_12
Patent number
US07846959B2

Reaction notes

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