Iodine → HCID 86682266, compound

HRID 540446Notes

Reaction equation

HRID 540446 reaction equation
II.Br[CH2:4][CH2:5][CH:6]=[CH2:7].[Br:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:10]=1/[CH:19]=[N:20]/[S:21]([C:23]([CH3:26])([CH3:25])[CH3:24])=[O:22]>C1COCC1>[Br:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:10]=1[C@@H:19]([NH:20][S:21]([C:23]([CH3:26])([CH3:25])[CH3:24])=[O:22])[CH2:7][CH2:6][CH:5]=[CH2:4]

Participants

5

Reactant 3

HCID 807IodineHCID 21241Homoallyl bromideHCID 89522283HCID 89522283, compound

Product 1

HCID 86682266HCID 86682266, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
40 °C

Procedure

To a 100 mL three-neck RBF equipped with stir bar and condenser was added Mg (excess), catalytic iodine, THF (20 mL), followed by 4-bromobut-1-ene (4.55 g, 33.7 mmol) in small increments. The mixture was heated to 40° C. for 1 hour. The reaction was cooled to room temperature and the freshly made Grignard reagent was added via syringe into a 250 mL RBF with N-{(E)-[2-bromo-5-(trifluoromethyl)phenyl]methylidene}-2-methylpropane-2-sulfinamide (8.0 g, 22.5 mmol) in THF (100 mL). Upon completion, the reaction was quenched with saturated aqueous NH4Cl and partitioned with ethyl acetate. The organic was dried over sodium sulfate, filtered, concentrated and purified by column chromatography to yield N-{(1S)-1-[2-bromo-5-(trifluoromethyl)phenyl]pent-4-en-1-yl}-2-methylpropane-2-sulfinamide (6.0 g, 14.6 mmol). 1H NMR (500 MHz, CDCl3) δ7.72 (m, 2H), 7.42 (d, J=8.2 Hz, 1H), 5.87 (m, 1H), 5.13 (m, 2H), 5.02 (m, 1H), 2.24 (m, 1H), 2.18 (m, 1H), 2.08 (m, 1H), 1.98 (m, 1H), 1.27 (s, 9H).

Workup

  1. customTo a 100 mL three-neck RBF equipped
  2. temperatureThe reaction was cooled to room temperature
  3. customUpon completion, the reaction was quenched with saturated aqueous NH4Cl
  4. custompartitioned with ethyl acetate
  5. dry with materialThe organic was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by column chromatography

Sources & evidence

ORD record
ord-aaceb2866daf474da000ff4d8b0c7090
Source dataset
uspto-grants-2014_10
Patent number
US08871738B2

Reaction notes

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