Benzyl Bromide → 3-Benzyl-5-methylbenzaldehyde

HRID 337656Notes

Reaction equation

HRID 337656 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[C:7]([CH3:9])[CH:8]=1)=[O:2].[F-].[Cs+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[CH2:15]([C:5]1[CH:4]=[C:3]([CH:8]=[C:7]([CH3:9])[CH:6]=1)[CH:1]=[O:2])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 25953Cesium fluorideHCID 16217687(3-Formyl-5-methylphenyl)boronic acid

Product 1

HCID 866516833-Benzyl-5-methylbenzaldehyde

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a DME solution (0.1 M) of (3-formyl-5-methylphenyl)boronic acid (1 eq.) was added cesium fluoride (3 eq.), tetrakis(triphenylphosphine)palladium (0.1 eq.) and benzyl bromide (1.2 eq.). The mixture was refluxed for 3 h, cooled down to RT and quenched with saturated aqueous sodium bicarbonate. The mixture was extracted with ethyl acetate. The combined organic extracts were then washed with brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product by way of flash chromatography (SiO2, Hex→7:3 (v/v) Hex:EtOAc) afforded the title compound.

Workup

  1. temperatureThe mixture was refluxed for 3 h
  2. customquenched with saturated aqueous sodium bicarbonate
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe combined organic extracts were then washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated in vacuo
  8. customPurification of the crude product by way of flash chromatography (SiO2, Hex→7:3 (v/v) Hex:EtOAc)

Sources & evidence

ORD record
ord-19fedb06d09447cf994a772536abab49
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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