Nitric Acid → HCID 86642843, compound

HRID 1667781Notes

Reaction equation

HRID 1667781 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][S:9]([CH3:12])(=[O:11])=[O:10])=[C:4]([CH2:13][OH:14])[CH:3]=1.[N+:15]([O-:18])(O)=[O:16]>S(=O)(=O)(O)O>[F:1][C:2]1[C:7]([N+:15]([O-:18])=[O:16])=[CH:6][C:5]([O:8][S:9]([CH3:12])(=[O:11])=[O:10])=[C:4]([CH2:13][O:14][S:9]([OH:11])(=[O:10])=[O:8])[CH:3]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 86642842HCID 86642842, compound

Product 1

HCID 86642843HCID 86642843, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To a mixture of 7.53 g (34 mmole) of methanesulfonic acid 4-fluoro-2-hydroxymethyl-phenyl ester and 60 mL of concentrated sulfuric acid at 0 degrees was added dropwise, a cold mixture of 2.5 mL of concentrated nitric acid and 3 mL of concentrated sulfuric acid. The mixture was poured on ice and extracted three times with 50 mL of ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was triturated with diethyl ether to give 3.5 g of methanesulfonic acid 4-fluoro-5-nitro-2-sulfooxymethyl-phenyl ester as a white solid. The white solid was heated to reflux for 1 hour with 100 mL of methanol, 2 mL of trimethylorthoformate and 0.10 g of p-toluenesulfonic acid monohydrate. The mixture was neutralized by addition of saturated sodium bicarbonate solution and then concentrated under reduced pressure. The residue was partitioned between 200 mL of ethyl acetate and 100 mL of saturated sodium bicarbonate solution. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 2.6 g of methanesulfonic acid 4-fluoro-2-hydroxymethyl-5-nitro-phenyl ester as a white solid.

Workup

  1. additionwas added dropwise
  2. additionThe mixture was poured on ice
  3. extractionextracted three times with 50 mL of ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-8b2543941c2a476db905000dd61c3a05
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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