Sulfuric Acid → HCID 69735150, compound

HRID 1814608Notes

Reaction equation

HRID 1814608 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][CH3:32])[C:28]([CH2:33]P(OCC)(OCC)=O)=[CH:27][C:26]=1[O:42][CH2:43][CH:44]([CH2:49][CH3:50])[CH2:45][CH2:46][CH2:47][CH3:48])(OCC)=O)C.[C:51](O[K])([CH3:54])([CH3:53])[CH3:52].S(=O)(=O)(O)O>O1CCCC1.C(OCC)(=O)C.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:24][C:25]2[CH:30]=[C:29]([O:31][CH3:32])[C:28]([CH:33]=[C:52]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:51]3[CH:54]=[CH:15][C:2]([Br:1])=[CH:3][CH:53]=3)=[CH:27][C:26]=2[O:42][CH2:43][CH:44]([CH2:49][CH3:50])[CH2:45][CH2:46][CH2:47][CH3:48])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 70304-BromobenzophenoneHCID 58887345HCID 58887345, compoundHCID 178418922HCID 178418922, compound

Product 1

HCID 69735150HCID 69735150, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Under an inert atmosphere, 4-bromobenzophenone (0.783 g, 3mmol), and 1,4-bis-(diethylphosphonomethyl)-2-(2-ethylhexyloxy)-5-methoxy benzene (0.660 g, 1.23 mmol) were dissolved in tetrahydrofuran (10 g). At room temperature, tetrahydrofuran (3.28 g) solution of tert-butoxy potassium (0.414 g, 3.69 mmol) was added dropwise for 5 minutes, and successively stirred for 3.5 hours. The reaction mixture was charged into water (100 ml) and neutralized with 5% sulfuric acid. After neutralization, ethyl acetate (250 ml) was added and the organic layer was partitioned. The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resultant raw product was purified by silica gel chromatography to give the desired product. (Yield: 0.86 g, 93%)

Workup

  1. customthe organic layer was partitioned
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resultant raw product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-f1ad3f57de03421082d4a0d31ddd2a74
Source dataset
uspto-grants-2005_04
Patent number
US06875895B2

Reaction notes

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