Iodine → Ethyl 2-(6-fluoro-1-hydroxy-1-indanyl)acetate

HRID 862755Notes

Reaction equation

HRID 862755 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 23293626Ethyl 2-(6-fluoro-1-hydroxy-1-indanyl)acetateYield 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%); NMR (DMSO-d6): d 6.99-7.24 (m, 3H, Ar), 5.38 (s, 1H, OH), 4.00 (q, 2H, CH2CH3), 2.64-2.92 (m, 4H, 2XCH2), 2.45-2.54, 2.05-2.14 (2m's, 2H, CH2CO), 1.08 (t,3H, CH3).

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-43e1f15fe6a143ef945e745c2b4e2794
Source dataset
uspto-grants-1998_02
Patent number
US05719186

Reaction notes

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