Sodium Bicarbonate → tert-Butyl 8-bromooctanoate

HRID 1978994Notes

Reaction equation

HRID 1978994 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10].ClC(Cl)(Cl)C(=N)O[C:16]([CH3:19])([CH3:18])[CH3:17].C(=O)(O)[O-].[Na+]>ClCCl.CCCCCC>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([O:11][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:10]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 5482758-Bromooctanoic acidHCID 2734700Tert-butyl 2,2,2-trichloroethanimidate

Product 1

HCID 10636360tert-Butyl 8-bromooctanoateYield 38%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent2×

Procedure

A 5.00 g (22.4 mmol) portion of 8-bromooctanoic acid was dissolved in a mixed solvent of 2 ml dichloromethane and 10 ml hexane, and the solution was mixed with 8.00 ml (44.8 mmol) of tert-butyl 2,2,2-trichloroacetoimidate and 0.45 ml (3.66 mmol) of boron trifluoride-ether complex and stirred at room temperature for 1 hour. The reaction solution was mixed with 10 ml of hexane and 0.031 g (3.66 mmol) of sodium bicarbonate, the resulting precipitate was separated by filtration, and then the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=5/1) to obtain 2.34 g (yield, 38%) of tert-butyl 8-bromooctanoate.

Workup

  1. customthe resulting precipitate was separated by filtration
  2. customthe solvent was evaporated under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-e1fb8cd6b4504a10be157cdcab070d8a
Source dataset
uspto-grants-2001_05
Patent number
US06239168B1

Reaction notes

Loading…