Bromobenzene → Ethyl 4-(4-bromophenyl)-4-methylpiperidine-1-carboxylate

HRID 1050543Notes

Reaction equation

HRID 1050543 reaction equation
O[C:2]1([CH3:13])[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.[Br:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.FC(F)(F)S(O)(=O)=O.[OH-].[Na+]>>[Br:14][C:15]1[CH:20]=[CH:19][C:18]([C:2]2([CH3:13])[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]2)=[CH:17][CH:16]=1

Participants

5

Reactant 4

HCID 7961BromobenzeneHCID 14798Sodium HydroxideHCID 62406Trifluoromethanesulfonic acidHCID 55277039Ethyl 4-hydroxy-4-methylpiperidine-1-carboxylate

Product 1

HCID 57489651Ethyl 4-(4-bromophenyl)-4-methylpiperidine-1-carboxylateYield 81.4%

Procedure

At 0° C. under N2 atmosphere, to a solution of ethyl 4-hydroxy-4-methylpiperidine-1-carboxylate (283) (2.4 g, 12.8 mmol) in bromobenzene (20.1 g, 128 mmol) was added trifluoromethanesulfonic acid (19.2 g, 128 mmol). The resulting mixture was stirred at RT for 3 hours before being poured onto ice. The mixture was basified with 1N NaOH and extracted with DCM (20 mL×3). The combined organic layers were washed with brine, dried, concentrated in vacuo and subjected to silica flash column using 0 to 20% EtOAc in PE to give ethyl 4-(4-bromophenyl)-4-methylpiperidine-1-carboxylate (284) (3.4 g, 81%) as a light yellow oil.

Workup

  1. additionbefore being poured onto ice
  2. extractionextracted with DCM (20 mL×3)
  3. washThe combined organic layers were washed with brine
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-54a516d4e487444683a93cba7aad2e4f
Source dataset
uspto-grants-2016_07
Patent number
US09382246B2

Reaction notes

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