Tetrahydrofuran → HCID 58099972, compound

HRID 383344Notes

Reaction equation

HRID 383344 reaction equation
C(=O)(OC)[O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:6](Br)=[CH:5][C:4]=1[CH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.F[C:22](F)(F)[B].[K].C(=O)([O-])[O-].[Cs+].[Cs+].O1CCCC1>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].O>[CH:13]1([C:4]2[CH:5]=[C:6]([CH3:22])[C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:3]=2[OH:2])[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 593949534-Bromo-2-cyclopentyl-5-nitrophenyl methyl carbonateHCID 87181123HCID 87181123, compound

Product 1

HCID 58099972HCID 58099972, compoundYield 52.1%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

To a microwave tube charged with 4-bromo-2-cyclopentyl-5-nitrophenyl methyl carbonate (500 mg, 1.45 mmol), Pd(dppf)Cl2 (96 mg, 0.13 mmol), potassium trifluoro-methyl-boron (177 mg, 1.45 mmol) and cesium carbonate (1420 mg, 4.36 mmol) was added tetrahydrofuran (2.5 mL) and water (1.25 mL). The reaction heated at 110° C. for 35 min under microwave irradiation. The reaction was partitioned between ethyl acetate and water. The organic layer was separated, dried over Na2SO4, filtered and concentrated in vacuo to yield a brown oil. Purification by silica gel chromatography (0-6% ethyl acetate/hexanes) provided 2-cyclopentyl-4-methyl-5-nitro-phenol (167 mg, 52% yield). 1H NMR (400.0 MHz, DMSO-d6) δ 10.08 (s, 1H), 7.43-7.38 (m, 1H), 7.22 (s, 1H), 3.28-3.21 (m, 1H), 2.43 (s, 3H), 1.96-1.91 (m, 2H), 1.80-1.51 (m, 6H).

Workup

  1. customThe reaction was partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto yield a brown oil
  7. customPurification by silica gel chromatography (0-6% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-f08b57a9670446159b3f48c34cc9ba5b
Source dataset
uspto-grants-2013_02
Patent number
US08367660B2

Reaction notes

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