Bromine → Tert-butyl 4-(2-bromo-4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-1-piperazinecarboxylate

HRID 1972445Notes

Reaction equation

HRID 1972445 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)=[CH:8][CH:7]=1)([OH:5])[CH3:4].[Br:27]Br>CCO>[Br:27][C:8]1[CH:7]=[C:6]([C:3]([OH:5])([CH3:4])[C:2]([F:1])([F:25])[F:26])[CH:11]=[CH:10][C:9]=1[N:12]1[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 24408BromineHCID 66582454Tert-butyl 4-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-1-piperazinecarboxylate

Product 1

HCID 66582356Tert-butyl 4-(2-bromo-4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-1-piperazinecarboxylateYield 62.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 500 mL round-bottomed flask was charged with tert-butyl 4-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-1-piperazinecarboxylate (8.61 g, 23.0 mmol) and 100 mL of EtOH. To this was added bromine (1.30 mL, 25.3 mmol). After 15 min, the reaction was concentrated and purified via column chromatography (120 g of silica, 0 to 40% EtOAc in hexanes) to give tert-butyl 4-(2-bromo-4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-1-piperazinecarboxylate (6.50 g) as a tan foam.

Workup

  1. concentrationthe reaction was concentrated
  2. custompurified via column chromatography (120 g of silica, 0 to 40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-f61ac16174f949d3a7484f5c8d5db5e2
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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