Water → Methyl 4-[(acetyloxy)methyl]-3-methylbenzoate

HRID 501803Notes

Reaction equation

HRID 501803 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][C:7]=1Br)(=[O:3])[CH3:2].O.[CH2:18](OCC)C>CN(C)P(N(C)C)(N(C)C)=O.C[Sn](C)(C)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:4][CH2:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][C:7]=1[CH3:18])(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 962WaterHCID 3283Diethyl EtherHCID 57543439Methyl 4-[(acetyloxy)methyl]-3-bromobenzoate

Product 1

HCID 68460449Methyl 4-[(acetyloxy)methyl]-3-methylbenzoate

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 11661TetramethyltinSolventHCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
70 °C

Procedure

5.30 g of methyl 4-[(acetyloxy)methyl]-3-bromobenzoate was dissolved in 50 mL of hexamethylphosphoramide, to which 6.6 mL of tetramethyltin and 0.26 g of bis(triphenylphosphine)-palladium(II) dichloride were added at room temperature in a stream of nitrogen, and this solution was stirred for 3 hours at 70° C. The reaction mixture was cooled to room temperature, and was added to a mixture of water and diethyl ether, and then the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure. The resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=5:1] to yield 4.17 g of methyl 4-[(acetyloxy)methyl]-3-methylbenzoate as brown oil.

Workup

  1. additionwere added at room temperature in a stream of nitrogen
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customthe organic phase was separated
  4. washAfter the resultant organic phase was washed with water
  5. dry with materiala saturated sodium chloride solution, the washed phase was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled out under reduced pressure
  7. customThe resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=5:1]

Sources & evidence

ORD record
ord-306d33e6cdb64af592d0789d16344254
Source dataset
uspto-grants-2010_08
Patent number
US07772285B2

Reaction notes

Loading…