N-bromobutanimide → (3S)-1-bromo-4-(4-fluorophenoxy)-3-hydroxy-1-butyne

HRID 1671737Notes

Reaction equation

HRID 1671737 reaction equation
[F:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][CH2:7][C@@H:8]([OH:11])[C:9]#[CH:10])=[CH:4][CH:3]=1.[Br:14]N1C(=O)CCC1=O>CC(C)=O.[N+]([O-])([O-])=O.[Ag+]>[Br:14][C:10]#[C:9][C@H:8]([OH:11])[CH2:7][O:6][C:5]1[CH:12]=[CH:13][C:2]([F:1])=[CH:3][CH:4]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 865887753-Butyn-2-ol, 1-(4-fluorophenoxy)-, (2S)-

Product 1

HCID 67096607(3S)-1-bromo-4-(4-fluorophenoxy)-3-hydroxy-1-butyne

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 180AcetoneSolvent

Procedure

A mixture of (3S)-4-(4-fluorophenoxy)-3-hydroxy-1-butyne (2.5 g, 14 mmol), N-bromosuccinimide (NBS) (2.74 g, 15.4 mmol) and AgNO3 (0.12 g, 0.7 mmol) in acetone (70 mL) was stirred at ambient temperature. The pale solution became cloudy over 30 minutes. The mixture was concentrated under vacuum and the resulting residue was filtered through a plug of silica gel (1×5 cm) eluted with 1:4 ethyl acetate:hexane to obtain (3S)-1-bromo-4-(4-fluorophenoxy)-3-hydroxy-1-butyne, a compound of formula (CC), as a pale yellow oil containing some ethyl acetate, 4.75 g (quant.); 1H NMR (CDCl3) δ3.95-4.15 (m, 2H),4.75 (m, 1H), 6.86 (m, 2H), 6.97 (m, 2H) ppm.

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. filtrationthe resulting residue was filtered through a plug of silica gel (1×5 cm)
  3. washeluted with 1:4 ethyl acetate

Sources & evidence

ORD record
ord-32fd5ddb7e59417293c800f6e299084b
Source dataset
uspto-grants-2011_08
Patent number
US07994346B2

Reaction notes

Loading…