Sulfuric Acid → HCID 67100100, compound

HRID 2078269Notes

Reaction equation

HRID 2078269 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.OS(O)(=O)=O.[Cl:20][C:21]1[C:22]([F:43])=[C:23]([C:27]([CH3:42])([CH3:41])[C:28]([CH:30]([C:36]([O:38]CC)=O)[C:31]([O:33][CH2:34][CH3:35])=[O:32])=[O:29])[CH:24]=[CH:25][CH:26]=1>>[Cl:20][C:21]1[C:22]([F:43])=[C:23]2[C:24]([C:36]([OH:38])=[C:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:28](=[O:29])[C:27]2([CH3:41])[CH3:42])=[CH:25][CH:26]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14812Phosphorus oxide (P4O10)HCID 67099707HCID 67099707, compound

Product 1

HCID 67100100HCID 67100100, compoundYield 60.6%

Procedure

P2O5 (12.5 g, 88.1 mmol) was mixed with concentrated H2SO4 (11.2 mL, 81.3 mmol) at 0° C., and the resulting mixture was stirred for 30 minutes. Diethyl 2-(2-(3-chloro-2-fluorophenyl)-2-methylpropanoyl)malonate (1.00 g, 2.48 mmol) was added to the reaction, and the resulting mixture was stirred at 25° C. for 1 hour. The resulting mixture was quenched with ice, and, on melting, was extracted with EtOAc (3×100 mL). The combined organic layers were washed with brine (100 mL), dried over MgSO4, concentrated, and dried in vacuo to give crude ethyl 7-chloro-8-fluoro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-carboxylate (0.470 g). MS m/e=313 (M+H)+.

Workup

  1. stirringthe resulting mixture was stirred at 25° C. for 1 hour
  2. customThe resulting mixture was quenched with ice
  3. extractionwas extracted with EtOAc (3×100 mL)
  4. washThe combined organic layers were washed with brine (100 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customdried in vacuo

Sources & evidence

ORD record
ord-7e78ed7723c24527ab277a4799de0908
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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