Chlorodifluoromethane → HCID 54222057, compound

HRID 1683128Notes

Reaction equation

HRID 1683128 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([O:16][CH3:17])[C:14]=1[OH:15])[C:8]([O:10][CH3:11])=[O:9].Cl[CH:19]([F:21])[F:20]>O1CCCC1>[CH3:17][O:16][C:13]1[CH:12]=[C:7]([CH:6]=[C:5]([O:4][CH3:3])[C:14]=1[O:15][CH:19]([F:21])[F:20])[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 6372Chlorodifluoromethane2×HCID 24758Sodium hydride2×HCID 70164Methyl Syringate

Product 1

HCID 54222057HCID 54222057, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (0.144 g, 6 mmol) was added portionwise to a solution of methyl 3,5-dimethoxy-4-hydroxy-benzoate (0.21 g, 1 mmol) in tetrahydrofuran (20 mL) cooled to 0° C. After 2 hours, chlorodifluoromethane (gas) was introduced by sparge for 10 minutes every 2 hours (5 times). After 18 hours, an additional portion of sodium hydride (0.048 g, 2 mmol) was added followed by chlorodifluoromethane (gas) sparge for 10 minutes. The reaction mixture was sealed and stirred for 3 weeks. The reaction mixture was cooled to -78° C. and methanol (5 mL) was added. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was separated, dried over MgSO4, filtered, and evaporated in vacuo to give the title compound.

Workup

  1. customby sparge for 10 minutes every 2 hours (5 times)
  2. waitAfter 18 hours
  3. customsparge for 10 minutes
  4. customThe reaction mixture was sealed
  5. temperatureThe reaction mixture was cooled to -78° C.
  6. additionmethanol (5 mL) was added
  7. customThe reaction mixture was partitioned between ethyl acetate and water
  8. customThe organic layer was separated
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-8fbce8e110254c03b0feb1452fccec94
Source dataset
uspto-grants-1997_06
Patent number
US05635510

Reaction notes

Loading…