2-Methyl-2-pentene → 5-bromo-2,3-dihydro-1H-indene-1-carboxylic acid

HRID 1962343

Reaction equation

HRID 1962343 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:11]/[O:12]C)/[CH2:6][CH2:5]2.CC(=CCC)C.Cl([O-])=[O:21].[Na+].P([O-])(O)(O)=O.[Na+]>C(O)(C)(C)C.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([C:11]([OH:12])=[O:21])[CH2:6][CH2:5]2

Participants

7

Reactant 4

HCID 122432-Methyl-2-penteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 58909702(E)-5-bromo-1-(methoxymethylene)-2,3-dihydro-1H-indene

Product 1

HCID 138400065-bromo-2,3-dihydro-1H-indene-1-carboxylic acidYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a solution of the product from Example 100, Part B (300 mg, 1.3 mmol) and 2-methyl-2-pentene (8 ml) in tert-butanol (32 ml) was added a solution of sodium chlorite (1.36 g, 0.12 mmol) in H2O (12 ml) containing sodium dihydrogen phosphate (1.07 g, 8.9 mmol) and the mixture was stirred vigorously for 20 min at room temperature. Solvents were concentrated in vacuo and the residue was diluted with H2O, extracted with EtOAc (3×), extracts combined, dried (Na2SO4), and concentrated in vacuo to give the title compound (180 mg, 56%).

Workup

  1. concentrationSolvents were concentrated in vacuo
  2. additionthe residue was diluted with H2O
  3. extractionextracted with EtOAc (3×)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4a587beca0ca49bd8cddf20c7ccf0692
Source dataset
uspto-grants-2013_04
Patent number
US08415351B2

Linked notes

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