Hydrochloric Acid → 6-Bromo-2,3-dihydro-1H-indene-1-carboxylic acid

HRID 1032261Notes

Reaction equation

HRID 1032261 reaction equation
[CH:1]1([C:10]([OH:12])=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[Br:13]Br.Cl>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[Br:13][C:7]1[CH:8]=[C:9]2[C:4]([CH2:3][CH2:2][CH:1]2[C:10]([OH:12])=[O:11])=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24408BromineHCID 857281H-Indene-1-carboxylic acid, 2,3-dihydro-

Product 1

HCID 123184846-Bromo-2,3-dihydro-1H-indene-1-carboxylic acid

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

By following the procedure of Tetsuya, et al. referenced in part A, the 6-bromo compound can be obtained. For example, to a stirred, ice-cooled mixture of 8.1 g (50 mmol) indane-1-carboxylic acid and 8.1 g of FeCl3 in 300 ml of CCl4 is added dropwise a solution of 8.8 g of Br2 in 100 ml methylene chloride over a 1 hour period. The mixture is stirred for 3 hours under cooling and then for 1.5 hours at room temperature. The mixture is poured into 500 ml of dilute HCl and extracted with CHCl3. The extract is washed with water, dried over anhydrous MgSO4 and concentrated under reduced pressure. The residue is crystallized from hexane to give 6-bromo-indane-1-carboxylic acid.

Workup

  1. customcan be obtained
  2. temperatureunder cooling
  3. waitfor 1.5 hours at room temperature
  4. extractionextracted with CHCl3
  5. washThe extract is washed with water
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is crystallized from hexane

Sources & evidence

ORD record
ord-3ab90ff520c0488893162bfcea150ff9
Source dataset
uspto-grants-1990_09
Patent number
US04957914

Reaction notes

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