1,4-Dibromobutane → 1-[1-Hydroxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]cyclopentanol

HRID 252690

Reaction equation

HRID 252690 reaction equation
[Mg].Br[CH2:3][CH2:4][CH2:5][CH2:6]Br.[OH:8][C:9]([C:18]([F:21])([F:20])[F:19])([C:14]([F:17])([F:16])[F:15])[C:10](OC)=[O:11].[Cl-].[NH4+]>O1CCCC1>[OH:8][C:9]([C:10]1([OH:11])[CH2:6][CH2:5][CH2:4][CH2:3]1)([C:18]([F:21])([F:20])[F:19])[C:14]([F:17])([F:16])[F:15]

Participants

6

Reactant 4

HCID 80561,4-DibromobutaneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 9877912Methyl 3,3,3-trifluoro-2-hydroxy-2-trifluoromethylpropionate

Product 1

HCID 589393171-[1-Hydroxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]cyclopentanolYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A flask was charged with 9.7 g of magnesium and 200 ml of tetrahydrofuran, to which 43.2 g of 1,4-dibromobutane was added dropwise at 60° C. After the completion of dropwise addition, the contents were stirred for one hour at 60° C., and 22.6 g of methyl 2-hydroxy-3,3,3-trifluoro-2-trifluoromethylpropionate was added dropwise below 50° C. The mixture was stirred for one hour at room temperature, after which an ammonium chloride aqueous solution was added. This was followed by ordinary work-up and vacuum distillation, obtaining 22.4 g of the target compound (yield 89%).

Workup

  1. additionwas added dropwise at 60° C
  2. additionAfter the completion of dropwise addition
  3. stirringThe mixture was stirred for one hour at room temperature
  4. distillationThis was followed by ordinary work-up and vacuum distillation

Sources & evidence

ORD record
ord-b31391d3bffb4b50a3e35a23f49ffb54
Source dataset
uspto-grants-2011_01
Patent number
US07868199B2

Linked notes

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