Water → HCID 59593483, compound

HRID 2367119Notes

Reaction equation

HRID 2367119 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=[O:11])=O)=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20].N1C=CC=CC=1.N1C(F)=NC(F)=NC=1[F:30].O>ClCCl>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]2([F:30])[C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[C:10](=[O:12])[O:11]2)=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 12664Cyanuric fluorideHCID 665622-(4-Chloro-3-nitrobenzoyl)benzoic acid

Product 1

HCID 59593483HCID 59593483, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(4-chloro-3-nitrobenzoyl)benzoic acid (6.76 g, 22.00 mmol) in anhydrous dichloromethane (35 ml) at 0° C. pyridine (1.80 ml, 22.00 mmol) was added, followed by the dropwise addition of cyanuric fluoride (2.0 ml, 24.20 mmol) in dichloromethane (4.0 mL). The reaction mixture was stirred for 100 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 it was washed with dichloromethane. The filtrate was partitioned with water and the dichloromethane layer was washed with water and it was dried over anhydrous sodium sulfate. Filtration and concentration provided 3-(4-chloro-3-nitrophenyl)-3-fluoro-2-benzofuran-1(3H)-one, (6.10 g, 90% yield) as a crystalline solid, which was used without further purification. 1H NMR (400 MHz, DMSO-d6): 8.34 (d, J=2 Hz, 1H), 8.20 (dd, J1=8 Hz, J2=0.8 Hz, 1H), 8.01-7.94 (m, 3H), 7.86 (td, J1=8 Hz, J2=1.2 Hz, 1H), 7.72 (d, J=7.6 Hz, 1H); MS (EI) for C14H7ClFlNO4: 306 (M−).

Workup

  1. custom0° C
  2. stirringwas stirred for 10 min at 0° C
  3. filtrationThe resulting slurry was filtered through a pad of Celite and it
  4. washwas washed with dichloromethane
  5. customThe filtrate was partitioned with water
  6. washthe dichloromethane layer was washed with water and it
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-2f451240bbd54882b65fe0f812e2a898
Source dataset
uspto-grants-2014_04
Patent number
US08697737B2

Reaction notes

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