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

HRID 2078504Notes

Reaction equation

HRID 2078504 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-4adbec656b1a4be2a2fd435be757d52f
Source dataset
uspto-grants-2011_04
Patent number
US07928255B2

Reaction notes

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