1,3-Dibromopropane → HCID 10590658, compound

HRID 2289123Notes

Reaction equation

HRID 2289123 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].[Br:14][CH2:15][CH2:16][CH2:17]Br.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:5]=[CH:6][C:7]=1[O:8][CH2:17][CH2:16][CH2:15][Br:14]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 10797559Methyl 2-(3-fluoro-4-hydroxyphenyl)acetate

Product 1

HCID 10590658HCID 10590658, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of methyl 3-fluoro-4-hydroxyphenylacetate (25.545 grams) in 2-butanone (300 mL) was treated with 1,3-dibromopropane (48.79 mL) and potassium carbonate (50.859 grams). The mixture was refluxed for 4 hours. The reaction mixture was partitioned between isopropyl acetate and pH 4 buffer. The organic was washed once with water, then dried over magnesium sulfate. The organic was filtered and evaporated to an oil which was chromatographed over silica gel with hexane/methylene chloride (2:1) to afford the title compound. This compound was taken forward without further purification.

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. customThe reaction mixture was partitioned between isopropyl acetate and pH 4 buffer
  3. washThe organic was washed once with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe organic was filtered
  6. customevaporated to an oil which
  7. customwas chromatographed over silica gel with hexane/methylene chloride (2:1)

Sources & evidence

ORD record
ord-131bbdbb36454241886e2ee18a5abdde
Source dataset
uspto-grants-2000_07
Patent number
US06090836

Reaction notes

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