Dimethyl Sulfate → HCID 13746653, compound

HRID 1731241Notes

Reaction equation

HRID 1731241 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:5]=1[CH:6]=[O:7])([OH:3])=[O:2].S(OC)(O[CH3:17])(=O)=O>C(Cl)Cl>[C:1]([C:4]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:5]=1[CH:6]=[O:7])([O:3][CH3:17])=[O:2]

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 202284174-fluoro-2-formylbenzoic acid2×

Product 1

HCID 13746653HCID 13746653, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred mixture of 3.4 g (0.02 mole) 2-carboxy-5-fluorobenzaldehyde (the product of Example 6) and 5.0 g [3.75 ml (0.04 mole)] dimethyl sulfate in methylene chloride was heated to reflux. The heating mantle was removed; and triethylamine, 4.15 g [5.7 ml (0.04 mole)] was added dropwise at a rate which maintained a brisk reflux. After the addition was complete, the reaction mixture was allowed to cool and was stirred at room temperature over the weekend. The reaction mixture was poured into water; the layers were separated. The methylene chloride layer was washed with a sodium bicarbonate solution, dried and evaporated to give 2.5 g of the above-identified product as a yellow oil.

Workup

  1. temperaturewas heated to reflux
  2. customThe heating mantle was removed
  3. additionand triethylamine, 4.15 g [5.7 ml (0.04 mole)] was added dropwise at a rate which
  4. temperaturemaintained a brisk reflux
  5. additionAfter the addition
  6. temperatureto cool
  7. additionThe reaction mixture was poured into water
  8. customthe layers were separated
  9. washThe methylene chloride layer was washed with a sodium bicarbonate solution
  10. customdried
  11. customevaporated

Sources & evidence

ORD record
ord-95505f1acacf46df8ae3d1bbab4893a6
Source dataset
uspto-grants-1986_11
Patent number
US04620867

Reaction notes

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