Trifluoroacetic acid → 5-bromo-4-fluoroisobenzofuran-1(3H)-one

HRID 2173193

반응식

HRID 2173193 반응식
[Br:1][C:2]1[C:3]([F:10])=[C:4]([CH2:8][OH:9])[CH:5]=[CH:6][CH:7]=1.FC(F)(F)[C:13]([O-])=[O:14].[Tl+].C(O)(C(F)(F)F)=O.[Cl-].[Li+].[O-2].[Mg+2]>[Pd](Cl)Cl.CCOC(C)=O.CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[C:13](=[O:14])[O:9][CH2:8][C:4]=2[C:3]=1[F:10]

참가 물질

9

반응물 5

HCID 6422Trifluoroacetic acidHCID 433294Lithium ChlorideHCID 6850729Magnesium monoxideHCID 21902506Thallium(1+);2,2,2-trifluoroacetateHCID 269856463-Bromo-2-fluorobenzyl Alcohol

생성물 1

HCID 666440385-bromo-4-fluoroisobenzofuran-1(3H)-one

시약·촉매·용매 3

HCID 24290Palladium Chloride촉매HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

To a flask charged with (3-bromo-2-fluorophenyl)methanol (840 mg, 4.1 mmol) and a stir bar was added added thallium trifluoroacetate (2.3 g, 4.3 mmol) and TFA (4.0 mL) at 0° C. The mixture was allowed to stir for 16 hours. LC showed no SM left at that point. The volatiles were removed under reduced pressure, and the residue was dissolved in DCM and concentrated twice to affect azeotropic removal of all TFA. After pumping the residue under high vacuum for 20 minutes, palladium chloride (73 mg, 0.41 mmol), lithium chloride (350 mg, 8.2 mmol), magnesium oxide (330 mg, 8.2 mmol), and MeOH (15 mL) were added to the flask. The mixture was treated under an atmosphere of CO for 2 hours. To this mixtue was added EtOAc to precipitate all the inorganic solids. The crude solution was filtered through a Celite® pad, and the filtrate was collected, adsorbed onto silica gel, and purified by silica gel chromatography. Removal of solvents gave rise to 5-bromo-4-fluoro-2-benzofuran-1(3H)-one. LC-MS (IE, m/z): 231 [M+1]+;

후처리

  1. additionwas added
  2. waitleft at that point
  3. customThe volatiles were removed under reduced pressure
  4. dissolutionthe residue was dissolved in DCM
  5. concentrationconcentrated twice
  6. customremoval of all TFA
  7. customfor 20 minutes
  8. additionThe mixture was treated under an atmosphere of CO for 2 hours
  9. customto precipitate all the inorganic solids
  10. filtrationThe crude solution was filtered through a Celite® pad
  11. customthe filtrate was collected
  12. custompurified by silica gel chromatography
  13. customRemoval of solvents

출처 및 근거

ORD 기록
ord-82abb59f38284675984ad59b56281b47
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056859B2

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