4-Bromophenol → trans-N-[4-(4-bromophenoxy)tetrahydrofuran-3-yl]propane-2-sulfonamide

HRID 2060824Notes

Reaction equation

HRID 2060824 reaction equation
CS([O:5][C@H:6]1[C@H:10]([NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH2:9][O:8][CH2:7]1)(=O)=O.[Br:18][C:19]1[CH:24]=[CH:23][C:22](O)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)(O)[O-].[Na+]>C(#N)C>[Br:18][C:19]1[CH:24]=[CH:23][C:22]([O:5][C@@H:6]2[CH2:7][O:8][CH2:9][C@H:10]2[NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 78084-BromophenolHCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 86653047HCID 86653047, compound

Product 1

HCID 67194484trans-N-[4-(4-bromophenoxy)tetrahydrofuran-3-yl]propane-2-sulfonamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a microwave vial, a solution of trans-4-[(isopropylsulfonyl)amino]tetrahydrofuran-3-yl methanesulfonate (546 mg, 1.90 mmol) in acetonitrile (8 mL) was combined with 4-bromophenol (97%, 407 mg, 2.28 mmol) and cesium carbonate (929 mg, 2.85 mmol). The reaction was irradiated in a microwave reactor at 160° C. for 2 hours, then cooled to room temperature and treated with saturated aqueous sodium bicarbonate solution (10 mL). The reaction was extracted with ethyl acetate and the combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (Gradient: 20% to 50% ethyl acetate in heptane), to afford trans-N-[4-(4-bromophenoxy)tetrahydrofuran-3-yl]propane-2-sulfonamide. Yield: 626 mg, 1.72 mmol, 91%. LCMS m/z 361.9 (M−1). 1H NMR (400 MHz, CDCl3) δ 1.38 (d, J=6.9 Hz, 3H), 1.40 (d, J=6.8 Hz, 3H), 3.19 (septet, J=6.8 Hz, 1H), 3.82 (br d, J=8.0, 1H), 3.91 (dd, J=10.6, 1.7 Hz, 1H), 4.02-4.08 (m, 2H), 4.24 (dd, J=10.5, 4.7 Hz, 1H), 4.85 (br d, J=4.7 Hz, 1H), 4.95 (br d, J=8.3 Hz, 1H), 6.88 (d, J=9.0 Hz, 2H), 7.40 (d, J=9.0 Hz, 2H). 13C NMR (100 MHz, CDCl3) δ 16.45, 16.71, 54.14, 58.70, 71.45, 71.81, 82.07, 113.97, 117.20, 132.52, 155.75.

Workup

  1. customThe reaction was irradiated in a microwave reactor at 160° C. for 2 hours
  2. extractionThe reaction was extracted with ethyl acetate
  3. dry with materialthe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography (Gradient: 20% to 50% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-a41e741df2464976890833fc646f5ef5
Source dataset
uspto-grants-2012_10
Patent number
US08278457B2

Reaction notes

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