2-(2-bromoethoxy)-1,3-dichlorobenzene → HCID 14407083, compound

HRID 1709878Notes

Reaction equation

HRID 1709878 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.Br[CH2:23][CH2:24][O:25][C:26]1[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][C:27]=1[Cl:33].CCCCCC.C(OCC)(=O)C>C(O)CCC>[F:21][C:18]1[CH:17]=[CH:16][C:15]([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH:9]2[CH2:14][CH2:13][N:12]([CH2:23][CH2:24][O:25][C:26]3[C:27]([Cl:33])=[CH:28][CH:29]=[CH:30][C:31]=3[Cl:32])[CH2:11][CH2:10]2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 24522402-(2-bromoethoxy)-1,3-dichlorobenzeneHCID 132505444-[Bis(4-fluorophenyl)methyl]piperidineHCID 21226206Ethyl acetate hexane

Product 1

HCID 14407083HCID 14407083, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 6.13 g (0.021 mole) of 4-[bis(4-fluorophenyl)methyl]piperidine, 5.38 g (0.03 mole) of 2-(2-bromoethoxy)-1,3-dichlorobenzene was heated overnight at gentle reflux in 200 ml of 1-butanol. The reaction mixture was filtered and stripped to dryness. The residue was dissolved in chloroform and extracted with water and 5% sodium hydroxide solution. The oil which was obtained was chromotagraphed on 300 g of silica gel using hexane-ethyl acetate (50/50 v/v) as eluant. The fractions containing product were combined and solvent removed to furnish an oil. The oil was dried overnight in vacuo at 80° C. This furnished 5.99 g (59%) of product oil.

Workup

  1. temperaturewas heated overnight
  2. filtrationThe reaction mixture was filtered
  3. dissolutionThe residue was dissolved in chloroform
  4. extractionextracted with water and 5% sodium hydroxide solution
  5. customThe oil which was obtained
  6. additionThe fractions containing product
  7. customsolvent removed
  8. customto furnish an oil
  9. customThe oil was dried overnight in vacuo at 80° C

Sources & evidence

ORD record
ord-4759777cfd3a4d8ab28f90080262c01b
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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