2-Cyclopenten-1-one → (3R)-3-[4-Bromo-3-(trifluoromethyl)phenyl]cyclopentanone

HRID 1627065Notes

Reaction equation

HRID 1627065 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](B2OC(C)(C)C(C)(C)O2)=[CH:4][C:3]=1[C:17]([F:20])([F:19])[F:18].CC(OC)(C)C.[C:27]1(=[O:32])[CH2:31][CH2:30][CH:29]=[CH:28]1>O1CCOCC1.O.C(N(CC)CC)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:29]2[CH2:30][CH2:31][C:27](=[O:32])[CH2:28]2)=[CH:4][C:3]=1[C:17]([F:18])([F:19])[F:20]

Participants

7

Reactant 3

HCID 135882-Cyclopenten-1-oneHCID 15413tert-Butyl methyl etherHCID 49834552HCID 49834552, compound

Product 1

HCID 49834553(3R)-3-[4-Bromo-3-(trifluoromethyl)phenyl]cyclopentanone

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8471TriethylamineSolventHCID 312751,4-DioxaneSolvent

Procedure

2-[4-bromo-3-(trifluoromethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3.0 g, 8.5 mmol) (Preparation 5) and [Rh(R-BINAP)(nbd)]BF4 (155 mg) were dissolved in a de-gassed solution of 2-cyclopenten-1-one (0.70 g) in 1,4-dioxane (12.8 mL), water (2.5 mL), and triethylamine (1.2 mL) in a microwave vial and irradiated in a microwave reactor at 120° C. for 5 min. MTBE was added and the mixture was washed 3 times with water. The organic phase was dried, concentrated under reduced pressure and purified by flash chromatography (100% heptane->70% EtOAc/Heptane) to obtain the title compound. 1H NMR (300 MHz, CDCl3) δ 7.68 (d, J=8.2, 1H), 7.57 (d, J=2.2, 1H), 7.28 (dd, J=8.4, 2.3, 1H), 3.51-3.36 (m, 1H), 2.76-2.64 (m, 1H), 2.56-2.23 (m, 4H), 2.06-1.89 (m, 1H).

Workup

  1. customirradiated in a microwave reactor at 120° C. for 5 min
  2. washthe mixture was washed 3 times with water
  3. customThe organic phase was dried
  4. concentrationconcentrated under reduced pressure
  5. custompurified by flash chromatography (100% heptane->70% EtOAc/Heptane)

Sources & evidence

ORD record
ord-4511e345e5c84b39822dccacddcd85a2
Source dataset
uspto-grants-2014_07
Patent number
US08785494B2

Reaction notes

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