Diisobutylaluminum hydride → HCID 67233948, compound

HRID 339685Notes

Reaction equation

HRID 339685 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([F:17])[CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12](OCC)=[O:13])[CH:8]=[CH:7]2.CC(C[AlH]CC(C)C)C>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([F:17])[CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH2:12][OH:13])[CH:8]=[CH:7]2

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 67234511HCID 67234511, compound

Product 1

HCID 67233948HCID 67233948, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Ethyl 8-bromo-6-fluoroquinoline-2-carboxylate (3.201 g, 10.7 mmol) was weighed into a flask, and dissolved in 100 mL of DCM. The reaction was cooled to −78° C., followed by drop-wise addition of DIBAL-H (21.48 mL, 32.22 mmol) over 10 minutes. The reaction was then allowed to stir and warm to ambient temperature over 2 hours at which time the starting material had been consumed. The reaction was quenched with 10 mL MeOH, followed by addition of 100 mL of Rochelle's Salts, and stirred overnight to remove the emulsion. The reaction was then partitioned with ethyl acetate. The combined organic fractions were concentrated in vacuo. The crude semi solid was purified by flash column chromatography (eluting with a 20-50% ethyl acetate/hexanes gradient), affording the desired product as an orange-yellow semi solid (2.27 g, 42% yield) MS APCI (+) m/z 256.1 and 258 (M+1 of each Br isotope) detected.

Workup

  1. temperaturewarm to ambient temperature over 2 hours at which time the starting material
  2. customhad been consumed
  3. customThe reaction was quenched with 10 mL MeOH
  4. additionfollowed by addition of 100 mL of Rochelle's Salts
  5. stirringstirred overnight
  6. customto remove the emulsion
  7. customThe reaction was then partitioned with ethyl acetate
  8. concentrationThe combined organic fractions were concentrated in vacuo
  9. customThe crude semi solid was purified by flash column chromatography (
  10. washeluting with a 20-50% ethyl acetate/hexanes gradient),

Sources & evidence

ORD record
ord-db3cc271795947f880443cfb2afc68e5
Source dataset
uspto-grants-2014_11
Patent number
US08895550B2

Reaction notes

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