Hydrochloric Acid → 2-Nitro-4-t-butoxycarbonyl-benzoylfluoride

HRID 965276Notes

Reaction equation

HRID 965276 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:6][C:5]=1[N+:17]([O-:19])=[O:18].[OH-].[Na+].Cl.N1C=CC=CC=1.N1C(F)=NC(F)=NC=1[F:32]>O1CCOCC1.C(Cl)Cl>[N+:17]([C:5]1[CH:6]=[C:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:8]=[CH:9][C:4]=1[C:3]([F:32])=[O:2])([O-:19])=[O:18]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 12664Cyanuric fluorideHCID 14798Sodium HydroxideHCID 23291046Tert-butyl 4-(methoxycarbonyl)-3-nitrobenzoate

Product 1

HCID 190761842-Nitro-4-t-butoxycarbonyl-benzoylfluoride

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of the above di-ester ((7), 7.28 g, 26 mmol) in dioxane (100 mL) was added aq. 1N NaOH (30 mL). The reaction was stirred for 6 h, acidified with aq. 1N HCl (30 mL), extracted with ethyl acetate, washed with brine, dried (MgSO4) and evaporated under reduced pressure to give the corresponding acid which was used as is in the next reaction. To a stirred solution of the above acid (6.68 g, 25 mMol) under Ar in dry CH2Cl2 (75 mL) was added pyridine (2.1 mL, 25 mMol) followed by cyanuric fluoride (1.56 mL, 17 mMol). After stirring for 2 h the reaction became a thick suspension. The reaction was then evaporated under reduced pressure, taken up in ether (150 mL) and filtered through a pad of celite to remove insoluble materials. The filtrate was washed with cold water, dried (MgSO4), filtered and evaporated under reduced pressure to give the crude acid fluoride (8) as a clear oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure
  5. customto give the corresponding acid which
  6. customas is in the next reaction
  7. stirringAfter stirring for 2 h the reaction
  8. customThe reaction was then evaporated under reduced pressure
  9. filtrationfiltered through a pad of celite
  10. customto remove insoluble materials
  11. washThe filtrate was washed with cold water
  12. dry with materialdried (MgSO4)
  13. filtrationfiltered
  14. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c34bde1f2c9d4eeb8fb3a7a607926471
Source dataset
uspto-grants-1998_06
Patent number
US05773512

Reaction notes

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