Iodine → HCID 86682273, compound

HRID 540450Notes

Reaction equation

HRID 540450 reaction equation
II.Br[CH2:4][CH2:5][CH2:6][CH:7]=[CH2:8].[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=1/[CH:20]=[N:21]/[S:22]([C:24]([CH3:27])([CH3:26])[CH3:25])=[O:23]>C1COCC1>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=1[C@@H:20]([NH:21][S:22]([C:24]([CH3:27])([CH3:26])[CH3:25])=[O:23])[CH2:8][CH2:7][CH2:6][CH:5]=[CH2:4]

Participants

5

Reactant 3

HCID 807IodineHCID 707041-Pentene, 5-bromo-HCID 89522283HCID 89522283, compound

Product 1

HCID 86682273HCID 86682273, compoundYield 53.8%

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 5-bromopent-1-ene (1.93 g, 12.9 mmol) added 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 (2.3 g, 6.5 mmol) in THF (20 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]hex-5-en-1-yl}-2-methylpropane-2-sulfinamide (1.5 g, 3.5 mmol). 1H NMR (500 MHz, CDCl3) δ7.71 (d, J=8.4 Hz, 1H), 7.63 (s, 1H), 7.41 (d, J=6.4 Hz, 1H), 5.77 (m, 1H), 5.03 (m, 2H), 4.87 (m, 1H), 3.65 (m, 1H), 2.11 (m, 2H), 1.86 (m, 1H), 1.82 (m, 1H), 1.55 (m, 1H), 1.40 (m, 1H), 1.22 (s, 9H).

Workup

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

Sources & evidence

ORD record
ord-b885e3897a6a4447b6ad9f4d3d4b33ef
Source dataset
uspto-grants-2014_10
Patent number
US08871738B2

Reaction notes

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