Ammonium Chloride → 4-[(Prop-2-en-1-yl)oxy]-3-(trifluoromethoxy)aniline

HRID 638925Notes

Reaction equation

[NH4+].[Cl-].[CH2:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:8]=1[O:16][C:17]([F:20])([F:19])[F:18])[CH:4]=[CH2:5]>CCO.O.C1COCC1.[Fe]>[CH2:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=1[O:16][C:17]([F:18])([F:19])[F:20])[CH:4]=[CH2:5]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of NH4Cl (3.3 g, 61.7 mmol) in EtOH (30.0 mL) and H2O (15.0 mL) at 90° C., was added a solution of 1-allyloxy-4-nitro-2-trifluoromethoxybenzene (1.6 g, 6.08 mmol) in THF (5.0 mL) followed by the addition of iron (1.02 g, 17.9 mmol, 3.0 equi) in two portions with 5 minutes interval. The resulting suspension was stirred at 90° C. for two hours then filtered through a pad of celite and the celite washed with EtOAc. The filtrate was diluted with H2O and extracted with EtOAc (3×70 mL). The combined organic layer was washed with aq. Na2CO3 (2×100 mL), brine (200 mL), dried over Na2SO4, and concentrated in vacuo to afford 4-allyloxy-3-trifluoromethoxyaniline (1.6 g). The product was used in the subsequent Step without further purification.

Workup

filtrationthen filtered through a pad of celite
washthe celite washed with EtOAc
additionThe filtrate was diluted with H2O
extractionextracted with EtOAc (3×70 mL)
washThe combined organic layer was washed with aq. Na2CO3 (2×100 mL), brine (200 mL)
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-22b931b8ace1492ab43c05544fc07f4c
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691843B2

Reaction notes

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