Benzene, 1-bromo-3-(trifluoromethyl)- → HCID 21096919, compound

HRID 1663028Notes

Reaction equation

HRID 1663028 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:3]=1.[NH:12]1[CH2:17][CH2:16][CH:15]([CH2:18][CH2:19][OH:20])[CH2:14][CH2:13]1.CC(C)([O-])C.[Na+].[OH-].[K+]>CO.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[F:9][C:8]([F:11])([F:10])[C:4]1[CH:3]=[C:2]([N:12]2[CH2:17][CH2:16][CH:15]([CH2:18][CH2:19][OH:20])[CH2:14][CH2:13]2)[CH:7]=[CH:6][CH:5]=1

Participants

8

Reactant 4

HCID 9817Benzene, 1-bromo-3-(trifluoromethyl)-HCID 14797Potassium HydroxideHCID 739534-PiperidineethanolHCID 23676156Sodium t-butoxide

Product 1

HCID 21096919HCID 21096919, compoundYield 45%

Reagents, catalysts & solvents 3

HCID 634876Binap, (A+-)-CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 887MethanolSolvent2×

Procedure

The process is performed as described in Example 2 (step 2.1). Starting with 25.6 g (113.90 mmol) of 1-bromo-3-(trifluoromethyl)benzene, 17.66 g (136.60 mmol) of 2-(4-piperidyl)ethanol, 26.24 g (273 mmol) of sodium tert-butoxide, 2.12 g (3.41 mmol) of BINAP and 1.04 g (1.14 mmol) of tris-(dibenzylideneacetone)dipalladium, and after chromatography on silica gel, eluting with a 25/75 mixture of ethyl acetate and cyclohexane, 17.90 g of an orange-coloured oily residue are obtained. This residue is then taken up in 100 ml of methanol, a solution of 4.24 g of potassium hydroxide in 15 ml of methanol is then added and stirring is continued at room temperature for 1 hour. The mixture is concentrated under reduced pressure and the residue is then taken up in chloroform and aqueous hydrochloric acid solution (1N). The organic phase is separated out and dried over sodium sulfate, and the filtrate is concentrated under reduced pressure. 14 g of product are obtained in the form of a dark yellow oil, which is used without further purification in the following step.

Workup

  1. washafter chromatography on silica gel, eluting with a 25/75 mixture of ethyl acetate and cyclohexane, 17.90 g of an orange-coloured oily residue
  2. customare obtained
  3. concentrationThe mixture is concentrated under reduced pressure
  4. customThe organic phase is separated out
  5. dry with materialdried over sodium sulfate
  6. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-976869096daf4c568c1421b7abb7e288
Source dataset
uspto-grants-2011_10
Patent number
US08034818B2

Reaction notes

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