Sulfuric Acid → HCID 55254012, compound

HRID 911215Notes

Reaction equation

HRID 911215 reaction equation
S(=O)(=O)(O)O.[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=1[CH:21]=[CH:22][N+:23]([O-])=O.[OH-].[Na+]>C1COCC1.O>[F:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=1[CH2:21][CH2:22][NH2:23]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 66692011HCID 66692011, compound

Product 1

HCID 55254012HCID 55254012, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Cautiously add sulfuric acid (14.7 mL, 265 mmol) dropwise at 0° C. to lithium aluminum hydride (1M solution in THF, 565 mL) with efficient stirring. Warm the mixture to ambient temperature for 20 min and then cool back to 0° C. Add a solution of 1-fluoro-4-methoxy-2-(2-nitro-vinyl)-benzene (18.7 g, 95 mmol) in THF (150 mL) by cannula and stir 2.5 h at ambient temperature. Cool the mixture to 0° C., cautiously add water (4.6 mL) followed by 2N aqueous NaOH (4.6 mL) and water (6.5 mL). Remove the precipitate by filtration and evaporate the filtrate to give the desired intermediate (16 g, 100%). MS (ES+) m/z: 170 (+H)+.

Workup

  1. customdropwise at 0° C.
  2. temperaturecool back to 0° C
  3. temperatureCool the mixture to 0° C.
  4. customRemove the precipitate
  5. filtrationby filtration
  6. customevaporate the filtrate

Sources & evidence

ORD record
ord-7d561f5358c84adb8d24b4a570afcfc4
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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