Hydrochloric Acid → 4-Chloro-3'-fluoro-6-(1-hydroxyethyl)-3-(2-oxoethyl)biphenyl-2-carbaldehyde

HRID 1192591Notes

Reaction equation

HRID 1192591 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([Cl:22])[C:7]([CH2:19][C:20]#N)=[C:8]([C:17]#N)[C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1)(=[O:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C.CCCCCC.Cl.[OH2:40].[OH-:41].[Na+]>C(Cl)Cl>[Cl:22][C:6]1[C:7]([CH2:19][CH:20]=[O:41])=[C:8]([CH:17]=[O:40])[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)=[C:4]([CH:1]([OH:3])[CH3:2])[CH:5]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 962WaterHCID 8058HexaneHCID 14798Sodium HydroxideHCID 21225700DiisobutylaluminumhydrideHCID 583685996-Acetyl-4-chloro-3-(cyanomethyl)-3'-fluorobiphenyl-2-carbonitrile

Product 1

HCID 583686864-Chloro-3'-fluoro-6-(1-hydroxyethyl)-3-(2-oxoethyl)biphenyl-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 6-acetyl-4-chloro-3-(cyanomethyl)-3′-fluorobiphenyl-2-carbonitrile (0.167 g, 0.534 mmol) in methylene chloride (2 mL) was added 1.0 M diisobutylaluminum hydride in hexane (2.9 mL, 2.9 mmol) at −78° C. The reaction was warmed to room temperature over 2 hours with stirring. Hydrogen chloride (5.0 M) in water (10 mL, 50 mmol) was added slowly and stirring was continued for 1 hour. Aqueous NaOH was used to render the solution alkaline, and the resulting mixture was extracted with dichloromethane. The combined organic layers were dried over sodium sulfate and evaporated to dryness. The residue was used in the next step. LCMS calculated for C17H12ClFO2 (M-18)+: m/z=302.1; Found: 302.1

Workup

  1. stirringstirring
  2. extractionthe resulting mixture was extracted with dichloromethane
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-9f473c803bb64d7a9dbb796e7b1d5228
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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