Benzyl Bromide → HCID 86639495, compound

HRID 1854715Notes

Reaction equation

HRID 1854715 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:14]=[O:15])[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.C(OCC)C>[CH2:22]([O:1][C:2]1[CH:3]=[C:4]([CH:14]=[O:15])[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 86639496HCID 86639496, compound

Product 1

HCID 86639495HCID 86639495, compoundYield 97.1%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4-hydroxybiphenyl-2-carboxaldehyde (80 mg, 0.40 mmol), potassium carbonate (111 mg, 0.80 mmol), and tetrabutylammonium iodide (15 mg, 0.04 mmol) in 0.8 mL of dry N,N-dimethylformamide was added benzyl bromide (72 μL, 0.60 mmol) at 0° C. After being stirred at room temperature overnight, the reaction mixture was diluted with diethyl ether. The solution was washed with water, saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 80/20) to obtain the title compound as a white crystal (112 mg, 77%).

Workup

  1. washThe solution was washed with water, saturated NaHCO3 aqueous solution, brine
  2. dry with materialdried over MgSO4
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated in vacuo
  5. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 80/20)

Sources & evidence

ORD record
ord-d25e9cce406f4b14b793980a71317417
Source dataset
uspto-grants-2015_02
Patent number
US08962674B2

Reaction notes

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