Dimethylformamide → 3-Phenylbenzaldehyde

HRID 23126

Reaction equation

HRID 23126 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:3]=1.C([Li])(C)(C)C.CN([CH:22]=[O:23])C>C1COCC1>[C:4]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=[C:2]([CH:22]=[O:23])[CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 164493-BromobiphenylHCID 178418306HCID 178418306, compound

Product 1

HCID 1210533-Phenylbenzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 1-bromo-3-phenylbenzene (Aldrich) (0.0858 moles) in 300 mL of dry THF cooled to −78° C. was added tert-butyl lithium (2 eq.) (1.7M in hexane) dropwise. The reaction mixture was stirred for 40 min. at −78° C. and then quenched with 2 eq. of DMF (13.24 mL). The resulting mixture was stirred for 20 min. and then poured into a separatory funnel and extracted with CH2Cl2. The organic extracts were washed with water, dried over Na2SO4, filtered and concentrated to give a brown oil. This oil was purified by LC 2000 chromatography, eluting with ethyl acetate/hexanes (5:95) to give 3-biphenylcarboxaldehyde.

Workup

  1. stirringThe resulting mixture was stirred for 20 min.
  2. additionpoured into a separatory funnel
  3. extractionextracted with CH2Cl2
  4. washThe organic extracts were washed with water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a brown oil
  9. customThis oil was purified by LC 2000 chromatography
  10. washeluting with ethyl acetate/hexanes (5:95)

Sources & evidence

ORD record
ord-519a9d6ea81e4572839e4452537a3aa9
Source dataset
uspto-grants-2005_02
Patent number
US06849650B2

Linked notes

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