Hydrochloric Acid → HCID 11369822, compound

HRID 1989822Notes

Reaction equation

HRID 1989822 reaction equation
[Br:1][C:2]1[C:3]([O:14][CH3:15])=[CH:4][C:5]([Cl:13])=[C:6]([C:8]([CH3:12])([CH3:11])[C:9]#N)[CH:7]=1.CC(C[AlH]CC(C)C)C.Cl.C1C[O:29]CC1>>[Br:1][C:2]1[C:3]([O:14][CH3:15])=[CH:4][C:5]([Cl:13])=[C:6]([C:8]([CH3:12])([CH3:11])[CH:9]=[O:29])[CH:7]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14487Diisobutylaluminum hydrideHCID 11392096HCID 11392096, compound

Product 1

HCID 11369822HCID 11369822, compound

Conditions

Temperature
0 °C

Procedure

A solution of 2-(5-bromo-2-chloro-4-methoxy-phenyl)-2-methyl-propionitrile (13 g, 0.045 mol) in dry THF (80 mL) was cooled to −10° C. under argon. DIBALH (1M in THF, 100 mL, 0.10 mol) was added keeping the temperature below 0° C. The mixture was stirred for 30 min/0° C. and then 2 h/25° C. The clear solution was carefully poured into icecold hydrochloric acid (2M, 100 mL). The THF was removed under reduced pressure. The aqueous phase was cooled and the crude product was filtered off and recrystallized from boiling MeOH. Yield: 7.8 g (59%). GCMS: >99%

Workup

  1. customthe temperature below 0° C
  2. custom2 h/25° C
  3. customThe THF was removed under reduced pressure
  4. temperatureThe aqueous phase was cooled
  5. filtrationthe crude product was filtered off
  6. customrecrystallized

Sources & evidence

ORD record
ord-3cc16568cda94b7388620af0faccd3a2
Source dataset
uspto-grants-2010_01
Patent number
US07642367B2

Reaction notes

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