Hydrochloric Acid → Methyl 4-chloro-3,5-diisopropoxybenzoate

Temperatur

65 °C

A suspension of copper (I) chloride (129 mg, 1.31 mmol) and tert-butyl nitrite (155 μL, 1.31 mmol) in anhydrous MeCN (2 mL) was stirred at 65° C. A solution of methyl 4-amino-3,5-diisopropoxybenzoate (4) (233 mg, 0.872 mmol) in anhydrous MeCN (1 mL) was added dropwise. Once the addition was complete the mixture was allowed to cool to RT and poured on to 20% HCl (5 mL). The mixture was partitioned between DCM (10 mL) and aq. ammonia (35%, 5 mL), the phases were separated and the organic solution was further washed with ammonia solution (17.5%, 10 mL), and brine (2×20 mL). The solvent was removed in vacuo and the residue was purified by silica gel chromatography (40 g, 0-100% EtOAc in isohexane) to afford methyl 4-chloro-3,5-diisopropoxybenzoate (93 mg, 36% yield) as a colourless oil: m/z 287 [M+H]+ (ES+).

1. additionOnce the addition
2. temperatureto cool to RT
3. customThe mixture was partitioned between DCM (10 mL) and aq. ammonia (35%, 5 mL)
4. customthe phases were separated
5. washthe organic solution was further washed with ammonia solution (17.5%, 10 mL), and brine (2×20 mL)
6. customThe solvent was removed in vacuo
7. customthe residue was purified by silica gel chromatography (40 g, 0-100% EtOAc in isohexane)

ORD-Eintrag

ord-ee66a503bb9b42dabd090455d8b78dc4

Quelldatensatz

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09447028B2