HCID 67099765, compound → HCID 67099861, compound

HRID 1868719Notes

Reaction equation

HRID 1868719 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:23])([CH3:22])[C:9]([CH:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12](OCC)=[O:13])=[O:10])=[CH:4][CH:3]=1>OS(O)(=O)=O>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[C:8]([CH3:22])([CH3:23])[C:9](=[O:10])[C:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:12]2[OH:13]

Participants

3

Reactant 1

HCID 67099765HCID 67099765, compound

Product 1

HCID 67099861HCID 67099861, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of the crude diethyl 2-(2-(4-bromophenyl)-2-methylpropanoyl)malonate (4982 mg, 12932 μmol) in concentrated H2SO4 (30 mL) was stirred at 23° C. After 2 hours, the reaction was poured into an ice-water mixture (200 mL) and extracted with EtOAc (3×200 mL). The combined organic layers were washed with brine (100 mL), dried over MgSO4, and concentrated in vacuo affording ethyl 6-bromo-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-carboxylate as the product.

Workup

  1. extractionextracted with EtOAc (3×200 mL)
  2. washThe combined organic layers were washed with brine (100 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-66620d4246a04f798658f06075816ed8
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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