Trisodium Phosphate → 2-Methoxyimino-3,3-diethoxy-4-bromobutyryl chloride

HRID 1154835Notes

Reaction equation

HRID 1154835 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH3:6][O:7][N:8]=[C:9]([C:13]([O:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])[CH2:14][Br:15])[C:10](O)=[O:11].P([O-])(O)(O)=O.[K+].P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+]>O1CCCC1.O.CN(C)C=O>[CH3:6][O:7][N:8]=[C:9]([C:13]([O:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])[CH2:14][Br:15])[C:10]([Cl:3])=[O:11]

Participants

8

Reactant 4

HCID 24243Trisodium PhosphateHCID 24813Phosphorus oxychlorideHCID 516951Monobasic potassium phosphateHCID 543237322-Methoxyimino-3,3-diethoxy-4-bromobutyric acid

Product 1

HCID 542161602-Methoxyimino-3,3-diethoxy-4-bromobutyryl chloride

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Phosphorus oxychloride (1.24 ml) was added to a solution of dry N,N-dimethylformamide (1.01 ml) in dry tetrahydrofuran (2ml ) at -20° C. and stirred at the same temperature for 30 minutes. To the solution was added 2-methoxyimino-3,3-diethoxy-4-bromobutyric acid (syn isomer, 3.3 g) at -20° C. and stirred at -20° to -10° C. for an hour. The resultant solution was added to a solution of potassium dihydrogenphosphate (3.63 g) and sodium phosphate (14.33 g) in water (1000 ml) and stirred under ice-cooling at pH 6.1 for 2 hours. The precipitates were collected by filtration, washed with water and dried to give 2-methoxyimino-3,3-diethoxy-4-bromobutyryl chloride (syn isomer, 3.0 g), mp 33°-35° C.

Workup

  1. stirringstirred at -20° to -10° C. for an hour
  2. stirringstirred under ice-
  3. temperaturecooling at pH 6.1 for 2 hours
  4. filtrationThe precipitates were collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-5537b6bb32624d0aa08b2d0700147df9
Source dataset
uspto-grants-1981_11
Patent number
US04298529

Reaction notes

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