Phenol → HCID 18687712, compound

HRID 1872871Notes

Reaction equation

HRID 1872871 reaction equation
[F:1][C:2]1[C:3]([S:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH:19]([CH3:21])[CH3:20])=[CH:14][C:13]=2[N+]([O-])=O)(=[O:11])=[O:10])=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C1(O)C=CC=CC=1.CC(C)([O-])C.[K+]>CN(C=O)C>[F:1][C:2]1[C:3]2[S:9](=[O:11])(=[O:10])[C:12]3[C:17](=[CH:16][C:15]([O:18][CH:19]([CH3:21])[CH3:20])=[CH:14][CH:13]=3)[O:8][C:4]=2[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 18687715HCID 18687715, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 18687712HCID 18687712, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

From 3-fluoro-2-((4-isopropoxy-2-nitrophenyl)sulphonyl)phenol (Example 21): A stirred solution of 3-fluoro-2-((4-isopropoxy-2-nitrophenyl))sulphonyl)phenol (0.35 g, 0.98 mmol) and potassium tert-butoxide (0.13 g, 1.18 mmol) in 25 mL anhydrous DMF was heated at 80° C. for 1 h during which time the reaction color changed from orange to light yellow. After the reaction had been cooled 10% aqueous HCL (100 mL) was added and the mixture extracted with EtOAc (2×100 mL). The combined organics were washed with 10% aqueous HCl (100 mL) and brine (100 mL), dried (Na2SO4) and concentrated in vacuo to a yellow solid (290 mg). Recrystallization from etOAC/hexane gave 210 mg (70%) of the title compound which was identical in all aspects to material prepared from 1-Fluoro-7-isopropoxyphenoxathiin (Example 20).

Workup

  1. temperatureAfter the reaction had been cooled 10% aqueous HCL (100 mL)
  2. additionwas added
  3. extractionthe mixture extracted with EtOAc (2×100 mL)
  4. washThe combined organics were washed with 10% aqueous HCl (100 mL) and brine (100 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo to a yellow solid (290 mg)
  7. customRecrystallization from etOAC/hexane

Sources & evidence

ORD record
ord-be29a06783b14d4fa287db725b0897dc
Source dataset
uspto-grants-2000_08
Patent number
US06110961

Reaction notes

Loading…