Dimethylformamide → 3-Phenylbenzaldehyde

HRID 636151Notes

Reaction equation

HRID 636151 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C([Li])(C)(C)C.CN(C)[CH:21]=[O:22]>C1COCC1>[C:8]1([C:4]2[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=2)[CH:21]=[O:22])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 164493-BromobiphenylHCID 178418306HCID 178418306, compound

Product 1

HCID 1210533-PhenylbenzaldehydeYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 3-bromobiphenyl (Aldrich; 1 molar eq.) in dry THF was cooled to −78° C. and treated with tert-butyllithium (Aldrich; 1.7 M in hexanes, 2 molar eq.) in a dropwise manner. The reaction was allowed to stir at −78° C. for 40 minutes. Dimethylformamide (Aldrich; 2.5 molar eq.) was added and stirring continued an additional 20 minutes. The mixture was partitioned in a separatory funnel between methylene chloride and water. The organic layer was dried over Na2SO4, filtered, and concentrated. The residue was purified via HPLC eluting with 5% ethyl acetate/hexanes. The desired aldehyde was obtained in 71% yield.

Workup

  1. stirringstirring
  2. waitcontinued an additional 20 minutes
  3. customThe mixture was partitioned in a separatory funnel between methylene chloride and water
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified via HPLC
  8. washeluting with 5% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-11a1a762949f4b2ab99c515898305b20
Source dataset
uspto-grants-2001_02
Patent number
US06191166B1

Reaction notes

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