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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1850080Generated: November 1, 2026

Hydrochloric Acid → 3-[[4-Methoxy-2′-(trifluoromethyl)[1,1′-biphenyl]-3-yl]oxy]azetidine

https://huagongshe.com/reaction/1850080

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantSodium BicarbonateHCID 516892—
ReactantHCID 67342335HCID 67342335—
SolventEthyl AcetateHCID 8857—
Solvent1,4-DioxaneHCID 31275—
ProductAmmonia methanolHCID 2170589710%
Product3-[[4-Methoxy-2′-(trifluoromethyl)[1,1′-biphenyl]-3-yl]oxy]azetidineHCID 46196448122.9%

Reaction Steps

To title compound of Step E (0.062 g, 0.146 mmol) in EtOAc (2 mL) was added 4M HCl in dioxane (2 mL). After 18 h, the reaction was neutralized with saturated NaHCO3 (aq.) and extracted with CH2Cl2 (2×). The combined organics were dried and concentrated. Silica gel chromatography (10-80% 2M NH3/MeOH in CH2Cl2) gave 0.029 g (61%) of the title compound. MS (ESI): mass calcd. for C17H16F3NO2, 323.11. m/z found, 324.2 [M+H]+. 1H NMR (CDCl3): 7.73 (d, J=7.8 Hz, 1H), 7.54 (t, J=7.3 Hz, 1H), 7.45 (t, J=7.6 Hz, 1H), 7.32 (d, J=7.6 Hz, 1H), 6.90 (td, J=8.2, 5.1 Hz, 2H), 6.59 (s, 1H), 5.02-4.97 (m, 1H), 3.92 (s, 3H), 3.96-3.85 (m, 7H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08957059B2
Source datasetuspto-grants-2015_02
ORD IDord-8bf33b46c60b463084aa58ee5a6f091d
Source noteuspto-grants-2015_02