2′-Bromo[1,1′-biphenyl]-4-carboxaldehyde → HCID 1394315, compound

HRID 1422337Notes

Reaction equation

HRID 1422337 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=1.[BH4-].[Na+]>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[CH:10][C:11]([CH2:12][OH:13])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 13927612′-Bromo[1,1′-biphenyl]-4-carboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 1394315HCID 1394315, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-(2'-bromophenyl)benzaldehyde 1.55 g, 7.95 mmol) in ethanol (15 mL) at 0° C. was added sodium borohydride (2.22 g, 58.7 mmol) and the reation stirred for 1 hour. The reaction was quenched with saturated aq. NH4Cl and extracted into diethyl ether. The organic extracts were washed with brine, dried, (Na2SO4) and evaporated in vacuo. The residue was purified by chromatography (Silica gel, 25% EtOAc in hexanes) to afford the title compound as a colourless oil.

Workup

  1. customThe reaction was quenched with saturated aq. NH4Cl
  2. extractionextracted into diethyl ether
  3. washThe organic extracts were washed with brine
  4. customdried
  5. custom(Na2SO4) and evaporated in vacuo
  6. customThe residue was purified by chromatography (Silica gel, 25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-9015b6a7c8b84a6f920c8287ce69a7e8
Source dataset
uspto-grants-2000_06
Patent number
US06080870

Reaction notes

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