Benzene → HCID 13015714, compound

HRID 1156796Notes

Reaction equation

HRID 1156796 reaction equation
[Cl:1][C:2]1[C:17]([Cl:18])=[C:16]([OH:19])[CH:15]=[CH:14][C:3]=1[C:4](=[N:12][OH:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1F.C1C=CC=CC=1.[H-].[Na+].Br[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>CN(C=O)C.C1(C)C=CC=CC=1.O>[O:13]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4]([C:3]2[CH:14]=[CH:15][C:16]([O:19][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:17]([Cl:18])[C:2]=2[Cl:1])=[N:12]1

Participants

8

Reactant 4

HCID 241BenzeneHCID 7748Ethyl bromoacetateHCID 24758Sodium hydride2×HCID 136359213HCID 136359213, compound

Product 1

HCID 13015714HCID 13015714, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 18.42 g (0.06 m) of 2,3-dichloro-4-hydroxy-2'-fluorobenzophenone oxime of Example 2C in 120 ml of DMF and 120 ml of benzene 3.6 g (0.15 m) of NaH is added. The mixture is brought to a temperature of 80°-85° C. and held there for 3 hours. The mixture is cooled to room temperature and a solution of 11 g (0.066 m) of ethyl bromoacetate in 20 ml of DMF is added dropwise. After addition the mixture is stirred for 1/2 hour. Water is added to decompose excess NaH. The mixture is extracted with ethylacetate, dried (Na2SO4) and evaporated to give 19 g. This is dissolved in toluene and chromatographed on silica gel with toluene as elutant. The product of ethyl 4-(1,2-benzisoxazol-3-yl)-2,3-dichlorophenoxyacetate is isolated from the column, 3.8 g (17%). An analytical sample is recrystallized from 95% ethanol, m.p. 88°-89° C.

Workup

  1. customis brought to a temperature of 80°-85° C.
  2. additionAfter addition the mixture
  3. extractionThe mixture is extracted with ethylacetate
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customto give 19 g
  7. customchromatographed on silica gel with toluene as elutant

Sources & evidence

ORD record
ord-3c6dc8856567482aa0c98ee7ed1065a4
Source dataset
uspto-grants-1982_06
Patent number
US04337261

Reaction notes

Loading…