Benzyl Bromide → HCID 86694927, compound

HRID 2204690Notes

Reaction equation

HRID 2204690 reaction equation
[C:1]([O:4][C:5]1[CH:14]=[C:13](C(Br)Br)[C:12]([Br:18])=[CH:11][C:6]=1C(OC)=O)(=O)[CH3:2].[C:19](=[O:22])([O-])[O-:20].[Ca+2].[C:24](=[O:27])([O-])[O-].[K+].[K+].[CH2:30](Br)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>O1CCOCC1.O.C(OCC)(=O)C>[Br:18][C:12]1[C:13]([CH:24]=[O:27])=[CH:14][C:5]([O:4][CH2:1][C:2]2[CH:13]=[CH:14][CH:5]=[CH:6][CH:11]=2)=[C:6]([CH:11]=1)[C:19]([O:20][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:22]

Participants

8

Reactant 4

HCID 7498Benzyl Bromide2×HCID 10112Calcium CarbonateHCID 11430Potassium Carbonate2×HCID 66611740HCID 66611740, compound

Product 1

HCID 86694927HCID 86694927, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of methyl 2-(acetyloxy)-5-bromo-4-(dibromomethyl)benzoate (may be prepared as described in Description 23; 1 g, 2.25 mmol) in 1,4-dioxane (5 ml) was added calcium carbonate (0.68 g, 6.74 mmol) and water (5 ml). The mixture was heated at 150° C. for 3 hours, cooled and the solvent was removed in vacuo. The residue was suspended in N,N-dimethylformamide (5 ml) and potassium carbonate (0.78 g, 5.62 mmol) and benzyl bromide (0.59 ml, 4.94 mmol) were added and the mixture was stirred for 18 hours. Ethyl acetate (15 ml) and water (10 ml) were added and the organic layer washed further with water (2×10 ml), dried (MgSO4) and the solvent removed in vacuo. Some starting material was still present. The residue was redissolved in N,N-dimethylformamide (5 ml) and potassium carbonate (0.78 g, 5.62 mmol) and benzyl bromide (0.59 ml, 4.94 mmol) were added and heated at 50° C. for 3 hours, cooled and the solvent was removed in vacuo. Purification by column chromatography (SiO2; 6:1 cyclohexane/ethyl acetate) yielded the title compound as an oil. 956 mg.

Workup

  1. temperaturecooled
  2. customthe solvent was removed in vacuo
  3. washthe organic layer washed further with water (2×10 ml)
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo
  6. dissolutionThe residue was redissolved in N,N-dimethylformamide (5 ml)
  7. temperatureheated at 50° C. for 3 hours
  8. temperaturecooled
  9. customthe solvent was removed in vacuo
  10. customPurification by column chromatography (SiO2; 6:1 cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-cbf483b2801e4a36857b8e6f83391b9b
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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