Benzyl Bromide → HCID 66931168, compound

HRID 511964Notes

Reaction equation

HRID 511964 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1.C([O-])([O-])=O.[K+].[K+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CC(C)=O.C(OCC)C>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 66931314HCID 66931314, compound

Product 1

HCID 66931168HCID 66931168, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 9.1 (0.9 g, 3.32 mmol) in anhydrous acetone (40 mL), was added anhydrous K2CO3 (1.38 g, 10 mmol) and benzyl bromide (0.624 g, 3.65 mmol) and the mixture was refluxed for 6 h. The reaction mixture was cooled to room temperature, diluted with acetone and solid materials were filtered off. The filtrate was evaporated under reduced pressure and the residue obtained was dissolved in diethyl ether (50 mL). The ethereal solution was washed with water and brine, dried (MgSO4) and evaporated. Purification by flash column chromatography on silica gel (5% Et2O-hexane) afforded 10.1 (0.938 g, 78% yield) as a white solid (m p 32-34° C.).

Workup

  1. temperaturethe mixture was refluxed for 6 h
  2. filtrationwere filtered off
  3. customThe filtrate was evaporated under reduced pressure
  4. customthe residue obtained
  5. washThe ethereal solution was washed with water and brine
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customPurification by flash column chromatography on silica gel (5% Et2O-hexane)

Sources & evidence

ORD record
ord-13ef9a8b009d413eab1f38b9e2b1dc4d
Source dataset
uspto-grants-2015_08
Patent number
US09102622B2

Reaction notes

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