1,4-Dibromobenzene → HCID 13207833, compound

HRID 434408Notes

Reaction equation

HRID 434408 reaction equation
BrCCBr.Br[C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][CH:7]=1.[F:13][C:14]1[CH:32]=[CH:31][C:17]2[C:18]([CH2:21][CH2:22][CH2:23][N:24]3[CH2:29][CH2:28][C:27](=[O:30])[CH2:26][CH2:25]3)=[N:19][O:20][C:16]=2[CH:15]=1.[Cl-].[NH4+]>C(OCC)C.O1CCCC1>[Br:12][C:9]1[CH:10]=[CH:11][C:6]([C:27]2([OH:30])[CH2:26][CH2:25][N:24]([CH2:23][CH2:22][CH2:21][C:18]3[C:17]4[CH:31]=[CH:32][C:14]([F:13])=[CH:15][C:16]=4[O:20][N:19]=3)[CH2:29][CH2:28]2)=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 78041,4-Dibromobenzene2×HCID 78391,2-DibromoethaneHCID 25517Ammonium ChlorideHCID 132078191-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-piperidone

Product 1

HCID 13207833HCID 13207833, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To 25 ml of ethyl ether was added 1.0 g of magnenesium turnings, 0.5 ml of 1,2-dibromoethane and a few drops of a solution of 9.4 g of 1,4-dibromobenzene in 50 ml of ethyl ether. The reaction was initiated with heat and maintained by the addition of the solution of 1,4-dibromobenzene. The resultant solution was stirred at ambient temperature for fifteen mins and then a solution of 7.0 g of 1-[3-(6-fluoro-1,2-benzisoxazol-3-yl)propyl]-4-piperidone in 50 ml of tetrahydrofuran was added with vigorous stirring. After the addition was complete, the mixture was stirred at ambient temperature for thirty mins and then poured into an ice cold solution of ammonium chloride. After dilution with 200 ml of ethyl ether, the organic layer was collected, washed with water (2×), saturated sodium chloride solution and then dried over anyhydrous magnesium sulfate. After filtering, the solvents were evaporated to an oil, which was triturated with petroleum ether. The resultant precipitate was collected and dried to give 4.4 g (41%) of product, mp 138°-145° C. Recrystallization four times from ethyl ether gave the analytical sample, mp 150°-151° C.

Workup

  1. temperaturewith heat
  2. additionAfter the addition
  3. customAfter dilution with 200 ml of ethyl ether, the organic layer was collected
  4. washwashed with water (2×), saturated sodium chloride solution
  5. dry with materialdried over anyhydrous magnesium sulfate
  6. filtrationAfter filtering
  7. customthe solvents were evaporated to an oil, which
  8. customwas triturated with petroleum ether
  9. customThe resultant precipitate was collected
  10. customdried

Sources & evidence

ORD record
ord-72c4ad97ff2747cd8c73ca7d0414a105
Source dataset
uspto-grants-1983_08
Patent number
US04396770

Reaction notes

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