p-Fluoronitrobenzene → HCID 69812241, compound

HRID 2381185Notes

Reaction equation

HRID 2381185 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[F:11][C:12]([F:24])([F:23])[CH:13]([O:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][O:18]1)[CH2:14][OH:15]>>[F:24][C:12]([F:11])([F:23])[CH:13]([CH2:14][O:15][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1)[O:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][O:18]1

Participants

3

Reactant 2

HCID 9590p-FluoronitrobenzeneHCID 22913409HCID 22913409, compound

Product 1

HCID 69812241HCID 69812241, compound

Procedure

On reaction of 1-fluoro-4-nitro-benzene and 3,3,3-trifluoro-2-(tetrahydro-pyran-2-yloxy)-propan-1-ol according to the procedure described in example 33 i) there was obtained 2-[2,2,2-trifluoro-1-(4-nitro-phenoxymethyl)-ethoxy]-tetrahydro-pyran. This compound was then treated with THF/1N HCl (20 min RT) to take off the tetrahydropyranyl protecting group and alkylated with methyl iodide in DMF and with NaH as a base at RT (2 h) to give 1-nitro-4-(3,3,3-trifluoro-2-methoxy-propoxy)-benzene, which was then hydrogenated as described in example 33 ii) to give the desired compound, (rac)-4-(3,3,3-trifluoro-2-methoxy-propoxy)-phenylamine.

Sources & evidence

ORD record
ord-db4cda970500435a94fb57096242d14e
Source dataset
uspto-grants-2012_09
Patent number
US08258158B2

Reaction notes

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