1-Fluoro-2-nitrobenzene → 2-Phenylethanol

HRID 1654546Notes

Reaction equation

HRID 1654546 reaction equation
N[CH:2]([OH:12])[CH2:3][C:4]1[C:9](Cl)=[CH:8][CH:7]=[CH:6][C:5]=1Cl.FC1C=CC=CC=1[N+]([O-])=O>>[C:4]1([CH2:3][CH2:2][OH:12])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 738951-Fluoro-2-nitrobenzeneHCID 18997263HCID 18997263, compound

Product 1

HCID 60542-Phenylethanol

Conditions

Temperature
110 °C

Procedure

A mixture of 1.03 g of α-amino-2,6-dichlorobenzeneethanol and 0.7 g of 1-fluoro-2-nitrobenzene was stirred for 3 hours at 110° C. The reaction mixture was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 98:2). The eluent of the desired fraction was evaporated and the residue was crystallized from acetonitrile. The product was filtered off and dried, yielding 0.4 g (24.4%) of (±)-2,6-dichloro-β-(2-nitrophenyl)amino]benzeneethanol; m.p. 127.6° C. (comp. 12).

Workup

  1. customThe reaction mixture was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 98:2)
  2. customThe eluent of the desired fraction was evaporated
  3. customthe residue was crystallized from acetonitrile
  4. filtrationThe product was filtered off
  5. customdried

Sources & evidence

ORD record
ord-41e3ba89edfd45e78af0ad1a979cd298
Source dataset
uspto-grants-1995_04
Patent number
US05407961

Reaction notes

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