Sodium Carbonate → 2-(Cyclopent-1-en-1-yl)-4-fluoro-1-methoxybenZene

HRID 471919

Reaction equation

HRID 471919 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[O:9][CH3:10].[C:11]1(B(O)O)[CH2:15][CH2:14][CH2:13][CH:12]=1.C([O-])([O-])=O.[Na+].[Na+]>C(#N)C.ClCCl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:11]1([C:2]2[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=2[O:9][CH3:10])[CH2:15][CH2:14][CH2:13][CH:12]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 1362922-Bromo-4-fluoroanisoleHCID 3861343(Cyclopent-1-en-1-yl)boronic acid

Product 1

HCID 593949342-(Cyclopent-1-en-1-yl)-4-fluoro-1-methoxybenZeneYield 49.2%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A microwave vial was charged with 2-bromo-4-fluoro-1-methoxybenzene (500 mg, 2.44 mmol), 1-cyclopentenylboronic acid (273 mg, 2.44 mmol), and Pd(dppf)Cl2 (199 mg, 0.24 mmol). The solids were dissolved in acetonitrile (7 mL) and 2 M Na2CO3 (5 mL) and the mixture heated under microwave irradiation for 20 min at 110° C. The reaction was diluted with dichloromethane (50 mL) and the layers separated. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated. Purification by silica gel chromatography (10-30% ethyl acetate/hexane) provided 2-cyclopentenyl-4-fluoro-1-methoxybenzene (231 mg, 49% yield). 1H NMR (400.0 MHz, DMSO-d6) δ 7.01 (dd, J=3.1, 10.0 Hz, 1H), 6.92-6.82 (m, 1H), 6.54 (dd, J=2.4, 6.5 Hz, 1H), 6.54 (s, 1H), 3.87 (s, 3H), 2.78-2.73 (m, 2H), 2.62-2.57 (m, 2H), 2.03-1.95 (m, 2H).

Workup

  1. customthe layers separated
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (10-30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-801f08fdadbf482e93767a63b1276d67
Source dataset
uspto-grants-2014_01
Patent number
US08633189B2

Linked notes

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