1-Bromo-4-(trifluoromethoxy)benzene → HCID 19040924, compound

HRID 866078Notes

Reaction equation

HRID 866078 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]1[CH2:12][CH2:11][CH:10]([C:13]([O:15]CC)=O)[CH2:9][CH2:8]1.[F:18][C:19]([F:29])([F:28])[O:20][C:21]1[CH:26]=[CH:25][C:24](Br)=[CH:23][CH:22]=1.[Mg]>O1CCCC1.CC(C)=O.C(Cl)Cl>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([C:13]([C:24]2[CH:23]=[CH:22][C:21]([O:20][C:19]([F:18])([F:28])[F:29])=[CH:26][CH:25]=2)([C:24]2[CH:25]=[CH:26][C:21]([O:20][C:19]([F:29])([F:28])[F:18])=[CH:22][CH:23]=2)[OH:15])[CH2:11][CH2:12]1

Participants

7

Reactant 3

HCID 5210081-Bromo-4-(trifluoromethoxy)benzeneHCID 764508HCID 764508, compoundHCID 5462224Magnesium

Product 1

HCID 19040924HCID 19040924, compoundYield 4.7%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent3×HCID 6344DichloromethaneSolvent3×HCID 8028TetrahydrofuranSolvent

Procedure

This compound was prepared in a manner analogous to that of Step B of Example 3, with 2.0 grams (0.008 mole) of ethyl N-(thien-2-ylmethyl)piperidin-4-ylcarboxylate, 3.5 mL (0.024 mole) of 4-trifluoromethoxyphenyl bromide, and 0.6 gram (0.025 gram-atom) of magnesium turnings in about 69 mL of tetrahydrofuran as reagents. The crude reaction product was subjected to column chromatography on silica gel, with pure methylene chloride, 9:1 methylene chloride:acetone, pure acetone, and then 8:2 methylene chloride:acetone as eluants. The product-containing fractions were combined and concentrated under reduced pressure, yielding about 0.2 gram of N-(thien-2-ylmethyl)-4-[bis(4-trifluoromethoxyphenyl)hydroxymethyl]piperidine. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customThis compound was prepared in a manner analogous to that of Step B of Example 3
  2. customThe crude reaction product
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0b4dfeb2292242cbbc852add7b738d1a
Source dataset
uspto-grants-1996_10
Patent number
US05569664

Reaction notes

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