Iodine → HCID 23293626, compound

HRID 362807Notes

Reaction equation

HRID 362807 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.Br[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].II>C(OCC)C.C1C=CC=CC=1.[Zn]>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[OH:11])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 807IodineHCID 7748Ethyl bromoacetateHCID 15194646-Fluoro-1-indanone

Product 1

HCID 23293626HCID 23293626, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 22174802Benzene etherSolvent

Procedure

A mixture of 6-fluoro-1-indanone (5.0 g, 33.3 mmol), ethyl bromoacetate (8.3 g, 50.0 mmol, Aldrich), activated zinc powder (3.2 g, 50.0 mmol, Mallinckrodt; Org. Synth., Coll. Vol. 6, 290, 1988) and a few crystals of iodine in diethyl ether-benzene (1:1, 100 mL) was heated at reflux under nitrogen for 24 h. The mixture was filtered and the filtrate was concentrated in vacuo. The residue in diethyl ether was vigorously stirred with excess dilute ammonium hydroxide, dried and concentrated to give ethyl 2-(6-fluoro-1-hydroxy-1-indanyl)acetate as an amber oil (7.6 g, 97%);

Workup

  1. temperatureat reflux under nitrogen for 24 h
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-dda5f779c25b4300b810346cbc832ce2
Source dataset
uspto-grants-1999_02
Patent number
US05872118

Reaction notes

Loading…