Sulfuric Acid → HCID 69735154, compound

HRID 1814613Notes

Reaction equation

HRID 1814613 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=O)=[CH:4][CH:3]=1.C(OP([CH2:24][C:25]1[CH:30]=[C:29]([O:31][CH2:32][CH3:33])[C:28]([CH2:34]P(OCC)(OCC)=O)=[CH:27][C:26]=1[O:43][CH2:44][CH3:45])(OCC)=O)C.[C:46](O[K])([CH3:49])([CH3:48])[CH3:47].S(=O)(=O)(O)O>O1CCCC1.O>[Br:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:34][C:28]2[CH:27]=[C:26]([O:43][CH2:44][CH3:45])[C:25]([CH:24]=[C:47]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:46]3[CH:49]=[CH:15][C:2]([Br:1])=[CH:3][CH:48]=3)=[CH:30][C:29]=2[O:31][CH2:32][CH3:33])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 70304-BromobenzophenoneHCID 2785335HCID 2785335, compoundHCID 178418922HCID 178418922, compound

Product 1

HCID 69735154HCID 69735154, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Under an inert atmosphere, 4-bromobenzophenone (2.611 g, 10 mmol), and 1,4-bis(diethylphosphonomethyl)-2,5-diethoxybenzene (1.912 g, 4.10 mmol) are dissolved in tetrahydrofuran (30 g). At room temperature, tetrahydrofuran (10.92 g) solution of tert-butoxy potassium (1.380 g, 12.30 mmol) is added dropwise for 5 minutes, and successively stirred for 3.5 hours. The reaction mixture is charged into water (200 ml) and neutralized with 5% sulfuric acid. After neutralization, a hydrophobic solvent is added and the organic layer is partitioned. The organic layer is washed with water and dried over anhydrous sodium sulfate. The solvent is distilled off under reduced pressure, and the resultant raw product is purified by silica gel chromatography or recrystallization to give a desired product.

Workup

  1. additionAfter neutralization, a hydrophobic solvent is added
  2. customthe organic layer is partitioned
  3. washThe organic layer is washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent is distilled off under reduced pressure
  6. customthe resultant raw product is purified by silica gel chromatography or recrystallization

Sources & evidence

ORD record
ord-95652d3e3c27438cb5239e863db58d97
Source dataset
uspto-grants-2005_04
Patent number
US06875895B2

Reaction notes

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