6-Oxabicyclo[3.1.0]hexane → trans-2-(4-Bromo-3-fluorophenoxy)cyclopentanol

HRID 2360307Notes

Reaction equation

HRID 2360307 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[F:9].[CH:10]12[O:15][CH:14]1[CH2:13][CH2:12][CH2:11]2.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)CCC>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C@@H:13]2[CH2:12][CH2:11][CH2:10][C@H:14]2[OH:15])=[CH:4][C:3]=1[F:9]

Participants

5

Reactant 3

HCID 92446-Oxabicyclo[3.1.0]hexaneHCID 10340Sodium CarbonateHCID 27791534-Bromo-3-fluorophenol

Product 1

HCID 67192636trans-2-(4-Bromo-3-fluorophenoxy)cyclopentanol

Reagents, catalysts & solvents 1

HCID 8008ButyronitrileSolvent

Procedure

4-Bromo-3-fluorophenol (8.00 g, 41.9 mmol) and 6-oxabicyclo[3.1.0]hexane (8.25 mL, 95.2 mmol) were combined in butyronitrile (5.0 mL) and treated with sodium carbonate (4.04 g, 38.1 mmol). The reaction was subjected to microwave irradiation for 2 hours at 175° C., then filtered through Celite®. The filter cake was washed with ethyl acetate, then dichloromethane, and the combined filtrates were concentrated under reduced pressure to provide product as a dark brown oil. This material was used without additional purification. Yield: 11.59 g, >41.9 mmol, assumed quantitative. 1H NMR (400 MHz, CDCl3) δ 1.61-1.89 (m, 5H), 2.02-2.24 (m, 2H), 4.30 (m, 1H), 4.46 (m, 1H), 6.63 (ddd, J=8.9, 2.8, 1.1 Hz, 1H), 6.73 (dd, J=10.5, 2.8 Hz, 1H), 7.40 (dd, J=8.9, 8.0 Hz, 1H).

Workup

  1. customirradiation for 2 hours at 175° C.
  2. filtrationfiltered through Celite®
  3. washThe filter cake was washed with ethyl acetate
  4. concentrationdichloromethane, and the combined filtrates were concentrated under reduced pressure
  5. customto provide product as a dark brown oil
  6. customThis material was used without additional purification

Sources & evidence

ORD record
ord-6e0328a53e0d4423a65c58675cd03a3a
Source dataset
uspto-grants-2014_04
Patent number
US08686043B2

Reaction notes

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