Hydrochloric Acid → HCID 86612272, compound

HRID 2355210Notes

Reaction equation

HRID 2355210 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:8][C:7]=1[Br:21].[H-].C([Al+]CC(C)C)C(C)C.CO.Cl>C(Cl)Cl>[C:15]1([S:12]([C:9]2[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][CH:3]=[O:2])=[C:7]([Br:21])[CH:8]=2)(=[O:13])=[O:14])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 21225700DiisobutylaluminumhydrideHCID 66917466HCID 66917466, compound

Product 1

HCID 86612272HCID 86612272, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 3-(4-benzenesulfonyl-2-bromo-phenyl)-propionic acid methyl ester (6.73 g, 17.6 mmol) in DCM (100 mL) was added diisobutyl aluminum hydride (1.0M in toluene, 17.6 mL) at −78° C. under Argon. The reaction was maintained at −78° C. for 90 minutes, and MeOH (7 mL ca.) was then added at −78° C. The mixture was allowed to warm to room temperature. HCl (2M) was added and the mixture was extracted twice with DCM. The combined organic extracts were washed with water, dried over Na2SO4, filtered and evaporated in vacuo. The residue was purified via flash chromatography (hexane/EtOAc, 8/2) affording 3-(4-benzenesulfonyl-2-bromo-phenyl)-propionaldehyde (4.57 g, 74% yield).

Workup

  1. temperatureto warm to room temperature
  2. extractionthe mixture was extracted twice with DCM
  3. washThe combined organic extracts were washed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified via flash chromatography (hexane/EtOAc, 8/2)

Sources & evidence

ORD record
ord-0da0bd16be284a91b8642257a4181399
Source dataset
uspto-grants-2010_07
Patent number
US07754759B2

Reaction notes

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