1-Bromo-3-chloropropane → HCID 14153974, compound

HRID 980815Notes

Reaction equation

HRID 980815 reaction equation
Br[CH2:2][CH2:3][CH2:4][Cl:5].[OH:6][C:7]1[CH:8]=[C:9]2[CH:12]([C:13]([N:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)=[O:14])[CH2:11][C:10]2=[CH:21][CH:22]=1.[OH-].[K+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[Cl:5][CH2:4][CH2:3][CH2:2][O:6][C:7]1[CH:8]=[C:9]2[CH:12]([C:13]([N:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)=[O:14])[CH2:11][C:10]2=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 14797Potassium HydroxideHCID 14153973HCID 14153973, compound

Product 1

HCID 14153974HCID 14153974, compound

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Tetrabutylammonium chloride (4.48 g) and 1-bromo-3-chloropropane (127.8 ml) are added to a stirred solution of 5-hydroxy-1-(1-piperidinylcarbonyl)benzocyclobutene (31.8 g) in methylene chloride (250 ml) and potassium hydroxide (18.85 g, 45% in H2O) which has been stirred vigorously under nitrogen for one hour. The reaction mixture is stirred at RT overnight, diluted with methylene chloride, extracted with H2O, sat'd aqueous NaCl and the organic layer dried over sodium sulfate. The solution is filtered, evaporated in vacuo and chromatographed (silica gel: ethyl acetate/hexane) yielding the desired product as an oil which is identified by NMR.

Workup

  1. stirringThe reaction mixture is stirred at RT overnight
  2. extractionextracted with H2O
  3. dry with materialthe organic layer dried over sodium sulfate
  4. filtrationThe solution is filtered
  5. customevaporated in vacuo
  6. customchromatographed (silica gel: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a5d393087b894e0db7360ad5fce0852d
Source dataset
uspto-grants-1987_01
Patent number
US04639442

Reaction notes

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