Benzyl Bromide → HCID 66868184, compound

HRID 1920661Notes

Reaction equation

HRID 1920661 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:13][CH2:14][CH2:15][OH:16].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[CH2:17]([O:16][CH2:15][CH2:14][CH2:13][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]([O:11][CH3:12])[C:5]=1[O:4][CH3:3])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 137587333-(2,3-Dimethoxyphenyl)propan-1-ol

Product 1

HCID 66868184HCID 66868184, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

2.50 g (62.5 mmol) NaH (60% in oil) were suspended under nitrogen in 70 ml dry THF and a solution of 7.1 g (36.2 mmol) 3-(2,3-dimethoxy-phenyl)-propan-1-ol (J. Org. Chem., 1987, 52, 1072) in 50 ml THF was added dropwise at 18° C. The resulting mixture was stirred for 30 minutes and then a solution of 6.81 g (39.8 mmol) benzylbromide in 30 ml THF was added dropwise and the mixture was stirred over night at 18° C. The reaction was quenched with 10 ml water and the organic solvent was evaporated under reduced pressure. The residue was dissolved in 200 ml of ethyl acetate and the organic layer was washed with water and brine, dried over Na2SO4 and evaporated in vacuo. The crude product was purified by column chromatography on silica gel (ethyl acetate/n-hexane 1:40) to afford 8 g (77%) of the desired product as a colorless oil.

Workup

  1. stirringthe mixture was stirred over night at 18° C
  2. customThe reaction was quenched with 10 ml water
  3. customthe organic solvent was evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in 200 ml of ethyl acetate
  5. washthe organic layer was washed with water and brine
  6. dry with materialdried over Na2SO4
  7. customevaporated in vacuo
  8. customThe crude product was purified by column chromatography on silica gel (ethyl acetate/n-hexane 1:40)

Sources & evidence

ORD record
ord-b3a307a5adea4d67badb37cb455f854a
Source dataset
uspto-grants-2012_05
Patent number
US08173609B2

Reaction notes

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