Water → HCID 21287219, compound

HRID 868532Notes

Reaction equation

HRID 868532 reaction equation
[Cl:1][C:2]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:3]=1[CH2:4][O:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8].O1CCOCC1.[Br:26]Br.O>C(OCC)C>[Br:26][CH:6]([O:5][CH2:4][C:3]1[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:2]=1[Cl:1])[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 312751,4-DioxaneHCID 21287217HCID 21287217, compound

Product 1

HCID 21287219HCID 21287219, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2-(2,4-Dichlorobenzyloxy)acetophenone (29.52 g, 100 mmole) was dissolved in a mixture of diethyl ether (100 ml) and 1,4-dioxane (100 mmole) and bromine (16 g, 100 mmole) was added dropwise over 1 hour. After stirring at the same temperature for additional 1 hour, water (200 ml) was added and the mixture was separated into layers. The aqueous layer was extracted with diethyl ether (200 ml). The organic layers were combined, washed with 1% aqueous solution of sodium bicarbonate (180 ml) and dired over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and a mixture of benzene/n-hexane was added to the residue to crystallize. The crystals were filtered off to obtain a crude product of the title compound (28.57 g). The crude product (1 g, 2.67 mmole) was recrystallized from benzene/n-hexane to obtain the title compoud (0.79 g, 79%), m.p. 89°-91° C.

Workup

  1. additionwas added dropwise over 1 hour
  2. customthe mixture was separated into layers
  3. extractionThe aqueous layer was extracted with diethyl ether (200 ml)
  4. washwashed with 1% aqueous solution of sodium bicarbonate (180 ml)
  5. distillationThe solvent was distilled off under reduced pressure
  6. additiona mixture of benzene/n-hexane
  7. additionwas added to the residue
  8. customto crystallize
  9. filtrationThe crystals were filtered off

Sources & evidence

ORD record
ord-c6d73fa70c5144aaa72a003496409d0c
Source dataset
uspto-grants-1988_10
Patent number
US04780471

Reaction notes

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