Hydrogen Bromide → HCID 18694036, compound

HRID 1603717Notes

Reaction equation

HRID 1603717 reaction equation
[Br:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[CH2:11][C:12]([O:14]C(C)(C)C)=[O:13])[C:3]1=[O:19].Br.O=C1C2C(=C(CC(O)=O)C=CC=2)CC1.BrBr>C(O)(=O)C.O>[Br:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[CH2:11][C:12]([OH:14])=[O:13])[C:3]1=[O:19]

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 24408BromineHCID 23237935HCID 23237935, compoundHCID 53693609HCID 53693609, compound

Product 1

HCID 18694036HCID 18694036, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

The (2-bromo-1-oxoindan-4-yl)acetic acid can be obtained in the following manner: 4 ml of hydrobromic acid at 47% are added to a solution of 38 g of (1-oxoindan-4-yl)acetic acid in 800 ml of acetic acid. 11 ml of bromine are added dropwise and over 10 minutes to this solution cooled to a temperature close to 15° C. and then the reaction medium is kept stirring for one hour at a temperature close to 15° C. The reaction medium is allowed to return to a temperature close to 20° C. and the reaction is continued for 2 hours. The reaction medium is poured into a mixture of 800 g of ice and 800 ml of water and then filtered on sintered glass. The filtrate is taken up in three times 800 ml of dichloromethane and the combined organic phases are washed with twice 800 ml of distilled water, dried over magnesium sulphate, filtered on paper and concentrated under reduced pressure at 50° C. The solid residue thus obtained is triturated in 240 ml of diisopropyl ether, filtered on sintered glass and air dried. 45.4 g of (2-bromo-1-oxoindan-4-yl)acetic acid are thus obtained in the form of a cream-coloured solid melting at 120° C.

Workup

  1. temperaturecooled to a temperature
  2. customclose to 15° C.
  3. customclose to 15° C
  4. customclose to 20° C.
  5. waitthe reaction is continued for 2 hours
  6. filtrationfiltered on sintered glass
  7. washthe combined organic phases are washed with twice 800 ml of distilled water
  8. dry with materialdried over magnesium sulphate
  9. filtrationfiltered on paper
  10. concentrationconcentrated under reduced pressure at 50° C
  11. customThe solid residue thus obtained
  12. customis triturated in 240 ml of diisopropyl ether
  13. filtrationfiltered on sintered glass and air
  14. customdried

Sources & evidence

ORD record
ord-711f93952cda459f92ddcae6aab11d70
Source dataset
uspto-grants-1999_11
Patent number
US05990108

Reaction notes

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