Réaction #1772041

Équation de réaction

3-bromobenzaldehyde

potassium tert-butoxide

THF

→

(E)-5-(3-bromophenyl)pent-4-enoic acid

Rendement 82.0%

Solvants

DMSO

DMSO

Conditions de réaction

Traitement

1. 1
   workup.WAITAfter several minutes a precipitate was observed
2. 2
   workup.ADDITIONThe solution was poured onto water (120 mL)
3. 3
   Lavagewashed with chloroform
4. 4
   Extractionextracted with chloroform (3×250 mL)
5. 5
   ConcentrationThe organic phase was concentrated
6. 6
   LavageGradient elution from 15-65% B (A=Hexanes

Mode opératoire

A 1M solution of potassium tert-butoxide in THF (80 mL) was added dropwise to (3-carboxypropyl)triphenylphosphoium bromide (17 g, 40 mmol) in anhydrous DMSO (20 mL) under nitrogen at 24° C., and the solution was stirred 30 min before addition of 3-bromobenzaldehyde (4.7 mL, 40 mmol). After several minutes a precipitate was observed and an additional 20 mL of DMSO was added to aid salvation, and the reaction was stirred 18 hours. The solution was poured onto water (120 mL) and washed with chloroform. The aqueous layer was acidified with conc. HCl and extracted with chloroform (3×250 mL). The organic phase was concentrated and applied to a 65 (M) Biotage® silica gel column; Gradient elution from 15-65% B (A=Hexanes; B=EtOAc) over 2 L to give Example 1, (E)-5-(3-bromophenyl)pent-4-enoic acid 8.2 g (82%). 1H NMR (300 MHz, CDCl3) δ 7.45 (t, J=1.5 Hz, 1H), 7.30 (dt, J=7.7, 1.5 Hz, 1H), 7.2-7.16 (m, 1H), 7.12 (t, J=7.7 Hz, 1H), 6.40-6.32 (m, 1H), 6.23-6.14 (m, 1H), 2.52 (s, 4H). RT=2.0 minutes (condition 1); LRMS: Anal. Calcd. for C11H11BrO2: 252.97. found: 252.98 (M−H).

Source