Carbon tetrabromide → HCID 54484537, compound

HRID 1369278Notes

Reaction equation

HRID 1369278 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12]O)=[C:8]([P:14]([O:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])=[O:15])[CH:7]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Br)(Br)(Br)[Br:43]>C1COCC1>[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][Br:43])=[C:8]([P:14]([O:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])=[O:15])[CH:7]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 57089632HCID 57089632, compound

Product 1

HCID 54484537HCID 54484537, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

3-(3-Diethoxyphosphoryl-4-hydroxymethyl-phenyl)propionic acid methyl ester (330 mg, 1 mmol), PPh3 (289 mg, 1.1 mmol) and CBr4 (365 mg, 1.1 mmol) were dissolved in 5 mL dry THF. The reaction mixture was stirred at 25° C. for 1 hr. The mixture turned cloudy. Solid was filtered and the filtrate was concentrated. The residue was further purified by flash column chromatography on silica gel (EtOAC/hexane 3/1, Rf=0.40). Pure product was obtained as an oil 150 mg (yield 38%).

Workup

  1. filtrationSolid was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was further purified by flash column chromatography on silica gel (EtOAC/hexane 3/1, Rf=0.40)

Sources & evidence

ORD record
ord-ba95d2936c72421992a639fc8719444f
Source dataset
uspto-grants-2003_06
Patent number
US06576766B1

Reaction notes

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