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Chemical Structure| 103438-90-0 Chemical Structure| 103438-90-0
Chemical Structure| 103438-90-0
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Product Details of [ 103438-90-0 ]

CAS No. :103438-90-0
Formula : C14H11FO2
M.W : 230.23
SMILES Code : O=CC1=CC=CC(OCC2=CC=CC=C2)=C1F
MDL No. :MFCD11110192

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Application In Synthesis of [ 103438-90-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 103438-90-0 ]

[ 103438-90-0 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 100-39-0 ]
  • [ 103438-86-4 ]
  • [ 103438-90-0 ]
YieldReaction ConditionsOperation in experiment
75% With sodium hydroxide; tetra-(n-butyl)ammonium iodide; In dichloromethane; water; 3-Hydroxy-2-fluorobenzaldehyde {reported by Kirk et. al., J. Med. Chem. 1986, 29, 1982} (15 g, 107 mmole) was added to an aqueous NaOH solution {(5.14 g, 128 mmole in water (50 mL)} and the mixture was stirred for 5 min to effect complete dissolution. To this was added a solution of benzyl bromide (16.46 g, 96.3 mmole) in methylene chloride (75 mL) followed by tetrabutylammonium iodide (0.5 g, 1.35 mmole) and vigorous stirring was continued overnight. The organic layer was separated and the aqueous layer was extracted with methylene chloride (100 mL). The combined organic layers were washed with 5% aqueous NaOH solution (2×25 mL) followed by water (50 mL) and finally with brine (20 mL). This solution was dried over anhydrous Na2SO4, filtered and evaporated to dryness. The resulting crude light yellow solid was crystallized from cyclohexane (150 mL) to afford the title compound (16.5 g, 75%); mp 88-89 C.
68% In N-methyl-acetamide; mineral oil; (i) 2-Fluoro-3-benzyloxybenzaldehyde 2-Fluoro-3-hydroxybenzaldehyde (16.49 g) was dissolved in dimethylformamide (200 ml) and stirred under an argon atmosphere. Sodium hydride was added (60% in mineral oil, 5.18 g) and the mixture was stirred for 30 minutes. Benzyl bromide was added (16.8 ml) and the mixture was stirred overnight. Reaction mixture was concentrated in vacuo and the resulting residue was partitioned between diethyl ether (200 ml) and water (200 ml). Combined organic extracts were washed with water (400 ml), dried (MgSO4) and concentrated in vacuo. The residue was purified by flash column chromatography, using a gradient of 0-10% ethyl acetate/iso-hexane as eluent to give the desired product as a yellow solid (18.41 g, 68%): 1H NMR (CD3SOCD3) delta 5.20 (s, 2H), 7.2-7.6 (m, 8H), 10.21(s, 1H)
(i) 2-Fluoro-3-benzyloxy benzaldehyde 2-Fluoro-3-hydroxybenzaldehyde (16.49 g) was dissolved in dimethylformamide (200 ml) and stirred under an argon atmosphere.. sodium hydride was added (60% in mineral oil, 5.18 g) and the mixture was stirred for 30 minutes.. benzyl bromide was added (16.8 ml) and the mixture was stirred overnight.. Reaction mixture was concentrated in vacuo and the resulting residue was partitioned between diethyl ether (200 ml) and water (200 ml).. Combined organic extracts were washed with water (400 ml), dried (MgSO4) and concentrated in vacuo.. The residue was purified by flash column chromatography, using a gradient of 0-10% ethyl acetate/iso-hexane as eluent to give the product as a yellow solid (18.41 g) 1H NMR (DMSO-d6) delta 5.20(s, 2H), 7.2-7.6(m, 8H), 10.21(s, 1H)
 

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