8-fluoro-3-methyl-octanoic acid synthesis

Yield:-

Steps:

Multi-step reaction with 8 steps
1: diisobutylaluminium hydride / toluene / 2 h / -78 °C
2: 1.) NaH / 1.) benzene, RT, 30 min, 2.) toluene, benzene, RT, overnight
3: 97 percent / p-toluenesulfonic acid / CH₂Cl₂ / 2 h / Ambient temperature
4: 68 percent / diethyl ether / 2 h
5: 90 percent / p-TsOH / methanol / 2 h / Ambient temperature
6: 87 percent / pyridine / CH₂Cl₂ / 12 h / Ambient temperature
7: 90 percent / n-Bu₄NF / tetrahydrofuran / 1.5 h / Ambient temperature
8: 96 percent / 1N aq.KOH / methanol / 0.17 h / Ambient temperature

References:

Nagatsuki, Fumi;Sasaki, Shigeki;Maeda, Minoru [Journal of Fluorine Chemistry,1992,vol. 56,# 3,p. 373 - 383]