Thiophenol → HCID 66756757, compound

HRID 1642638Notes

Reaction equation

HRID 1642638 reaction equation
[H-].[Na+].[C:3]1([SH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:10]([O:17][C:18]1[CH:23]=[C:22](F)[CH:21]=[CH:20][C:19]=1[N+:25]([O-:27])=[O:26])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(OCC)(=O)C>CN(C=O)C>[CH2:10]([O:17][C:18]1[CH:23]=[C:22]([S:9][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH:21]=[CH:20][C:19]=1[N+:25]([O-:27])=[O:26])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 7969ThiophenolHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 110969082-(Benzyloxy)-4-fluoro-1-nitrobenzene

Product 1

HCID 66756757HCID 66756757, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 60% suspension of sodium hydride in mineral oil (490 mg, 12.2 mmol) is stirred in 15 mL of DMF. To this mixture is carefully added benzenethiol (1.25 mL, 1.34 g, 12.2 mmol) and the mixture stirred for 1 h. To this solution is added portionwise 2-benzyloxy-4-fluoronitrobenzene (3.00 g, 12.1 mmol), giving initially a dark solution that eventually changed to pale yellow. When LC shows disappearance of starting material, the mixture is poured into ethyl acetate and extracted with water, 1N sodium hydroxide, and four times with brine. This solution is dried, filtered, and solvent removed under reduced pressure to leave a heterogeneous mixture that is triturated with hexane, filtered, and the solids washed with hexane to afford 2-benzyloxy-1-nitro-4-phenylsulfanylbenzene, mp 77-79° C.: NMR (CDCl3) δ 7.79 (d, 1H, J=8.6 Hz), 7.46 (m, 5H), 7.33 (m, 5H), 6.77 (d, 1H, J=1.8 Hz), 6.72 (dd, 1H, J=8.6, 1.8 Hz), 5.08 (s, 2H).

Workup

  1. customgiving initially a dark solution that
  2. extractionextracted with water, 1N sodium hydroxide, and four times with brine
  3. customThis solution is dried
  4. filtrationfiltered
  5. customsolvent removed under reduced pressure
  6. customto leave a heterogeneous mixture that
  7. customis triturated with hexane
  8. filtrationfiltered
  9. washthe solids washed with hexane

Sources & evidence

ORD record
ord-32664274d31c4ac4942af6f09dc27a92
Source dataset
uspto-grants-2012_02
Patent number
US08119666B2

Reaction notes

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