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

HRID 1354492Notes

Reaction equation

HRID 1354492 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) δ 3.95–4.15 (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-4a507754d8a0410687a5d5475e8e8e89
Source dataset
uspto-grants-2007_05
Patent number
US07223798B2

Reaction notes

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