Allyl bromide → HCID 118590516, compound

HRID 1054458Notes

Reaction equation

HRID 1054458 reaction equation
[In].[C:2]([S:6]([NH2:8])=[O:7])([CH3:5])([CH3:4])[CH3:3].[F:9][C:10]1[CH:11]=[CH:12][C:13]([O:18][CH:19]2[CH2:23][CH2:22][O:21][CH2:20]2)=[C:14]([CH:17]=1)[CH:15]=O.Br[CH2:25][CH:26]=[CH2:27]>C1COCC1.O>[F:9][C:10]1[CH:11]=[CH:12][C:13]([O:18][CH:19]2[CH2:23][CH2:22][O:21][CH2:20]2)=[C:14]([C@H:15]([NH:8][S@:6]([C:2]([CH3:5])([CH3:4])[CH3:3])=[O:7])[CH2:27][CH:26]=[CH2:25])[CH:17]=1

Participants

7

Reactant 4

HCID 7841Allyl bromideHCID 3382465Tert-ButanesulfinamideHCID 5359967IndiumHCID 107697243HCID 107697243, compound

Product 1

HCID 118590516HCID 118590516, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of Indium powder (27 g, 235 mmol), S-tert-butyl sulfinamide (26.3 g, 216 mmol), 5-fluoro-2-((tetrahydrofuran-3-yl)oxy)benzaldehyde (38.0 g, 181 mmol) and Ti(OEt)4 (61.8 g, 271 mmol) in THF (380 mL) was refluxed for 2 h. Reaction mass was cooled to 0° C. and added 3-bromoprop-1-ene (28.4 g, 235 mmol) slowly for a period of 30 min. Reaction mass was heated to reflux for 16 h, cooled to room temperature and diluted with water (1.0 L), the hazy solution was filtered through celite bed and the solids were washed with ethyl acetate (1.0 L). The filtrate was extracted with ethyl acetate (600 ml). The combined organic phases were washed with water and brine which was dried over Na2SO4 and concentrated to get the desired product as viscous liquid. This was purified over 60-120 mesh silica using 50-60% ethyl acetate and hexane as an eluent to get the pure product (30 g, yield: 47%). MS (ESI): m/z 356.45 (M+H)

Workup

  1. temperaturewas refluxed for 2 h
  2. customReaction mass
  3. customReaction mass
  4. temperaturewas heated
  5. temperatureto reflux for 16 h
  6. temperaturecooled to room temperature
  7. filtrationthe hazy solution was filtered through celite bed
  8. washthe solids were washed with ethyl acetate (1.0 L)
  9. extractionThe filtrate was extracted with ethyl acetate (600 ml)
  10. washThe combined organic phases were washed with water and brine which
  11. dry with materialwas dried over Na2SO4
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-a75e908e12f146d7bbf0af299cd3d373
Source dataset
uspto-grants-2016_07
Patent number
US09394305B2

Reaction notes

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