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

HRID 2307606Notes

Reaction equation

HRID 2307606 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-18d25bd7be974fc1b2a8334ea07add7b
Source dataset
uspto-grants-2004_12
Patent number
US06831186B2

Reaction notes

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