3-Fluorophenol → Nitro-4-(3-fluoro-phenoxymethyl)-benzene

HRID 1827385Notes

Reaction equation

HRID 1827385 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][OH:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:31][C:32]1[CH:33]=[C:34](O)[CH:35]=[CH:36][CH:37]=1>O1CCCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:36]2[CH:35]=[CH:34][CH:33]=[C:32]([F:31])[CH:37]=2)=[CH:10][CH:11]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 97433-FluorophenolHCID 11776TriphenylphosphineHCID 692754-Nitrobenzyl alcohol

Product 1

HCID 22137955Nitro-4-(3-fluoro-phenoxymethyl)-benzeneYield 78.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2.0 g (13 mmol) 4-nitrobenzyl alcohol and 3.60 g (13.7 mmol) triphenylphosphine in 30 ml tetrahydrofurane is treated with 1.54 g (13.7 mmol) of 3-fluorophenol. The mixture is cooled in an ice-bath and 2.39 g (13.7 mmol) of diethyl-aza-dicarboxylate is slowly added. The ice-bath is removed and the reaction mixture stirred over night at room temperature. The tetrahydrofuran is evaporated, the oily residue triturated with diethyl ether, filtered and concentrated. Chromatography (silica gel, ethyl acetate/hexane 1:9) yields 2.52 g (78%) of the title compound as a slightly yellow solid. MS: m/e=247.1 (M++H).

Workup

  1. temperatureThe mixture is cooled in an ice-bath
  2. customThe ice-bath is removed
  3. customThe tetrahydrofuran is evaporated
  4. customthe oily residue triturated with diethyl ether
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ec75381d77b74dd780f41346afa305e6
Source dataset
uspto-grants-2006_05
Patent number
US07053245B2

Reaction notes

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