Acetonitrile → 5-Amino-4-fluoro-2-(1-methylcyclohexyl)phenol

HRID 73981

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH3:9][C:10]1(O)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.CC#[N:19]>>[NH2:19][C:3]1[C:2]([F:1])=[CH:7][C:6]([C:10]2([CH3:9])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[C:5]([OH:8])[CH:4]=1

Participants

Reactant 3

HCID 6342Acetonitrile

HCID 97324-Fluorophenol

HCID 115501-Methylcyclohexanol

Product 1

HCID 574702215-Amino-4-fluoro-2-(1-methylcyclohexyl)phenol

Procedure

5-Amino-4-fluoro-2-(1-methylcyclohexyl)phenol (C-13) was synthesized following the general scheme above starting from 4-fluorophenol and 1-methylcyclohexanol. Overall yield (3%). HPLC ret. time 3.00 min, 10-99% CH3CN, 5 min run; ESI-MS 224.2 m/z (MH+).

Workup

customOverall yield (3%)

Sources & evidence

ORD record: ord-b0069589c92348c584bf7e32e8626a12
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08829204B2

Linked notes

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