Triethylamine → HCID 11386998, compound

HRID 2079492Notes

Reaction equation

HRID 2079492 reaction equation
[P:1]([OH:31])([OH:30])([O:3][C:4]1[CH:9]=[C:8]([CH2:10][S:11]([CH:14]=[CH:15][C:16]2[C:21]([O:22][CH3:23])=[CH:20][C:19]([O:24][CH3:25])=[CH:18][C:17]=2[O:26][CH3:27])(=[O:13])=[O:12])[CH:7]=[CH:6][C:5]=1[O:28][CH3:29])=[O:2].C(Br)(Br)(Br)Br.[CH2:37](N(CC)CC)[CH3:38].P([O-])(OCC)O[CH2:46][CH3:47]>C(#N)C>[P:1]([O:31][CH2:46][CH3:47])([O:30][CH2:37][CH3:38])([O:3][C:4]1[CH:9]=[C:8]([CH2:10][S:11](/[CH:14]=[CH:15]/[C:16]2[C:17]([O:26][CH3:27])=[CH:18][C:19]([O:24][CH3:25])=[CH:20][C:21]=2[O:22][CH3:23])(=[O:13])=[O:12])[CH:7]=[CH:6][C:5]=1[O:28][CH3:29])=[O:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11205Carbon tetrabromideHCID 3780918DiethylphosphiteHCID 72273290HCID 72273290, compound

Product 1

HCID 11386998HCID 11386998, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 5-((2,4,6-trimethoxystyrylsulfonyl)methyl)-2-methoxyphenyl dihydrogen phosphate (1.9 g, 4.8 mmol) in acetonitrile (24 mL) at room temperature, was added carbon tetrabromide (1.94 g, 1.22 eq) and triethylamine (0.728 g, 1.5 eq). The resulting mixture was stirred for 10 minutes and than cooled to 0° C. in an ice-water bath. Diethyl phosphite (1.51 g, 1.2 eq) dissolved in acetonitrile (16 mL) was added dropwise to the cooled reaction mixture. The reaction mixture was stirred for 2 h and monitored by TLC. The reaction was terminated by dropwise addition of aqueous potassium dihydrogen phosphate (10 mL, 0.5 M). The resulting mixture was extracted with ethyl acetate (3×30 mL). The combined organic extract was dried (Na2SO4) and concentrated in vacuo to yield the desired product.

Workup

  1. additionwas added dropwise to the cooled reaction mixture
  2. stirringThe reaction mixture was stirred for 2 h
  3. customThe reaction was terminated by dropwise addition of aqueous potassium dihydrogen phosphate (10 mL, 0.5 M)
  4. extractionThe resulting mixture was extracted with ethyl acetate (3×30 mL)
  5. extractionThe combined organic extract
  6. dry with materialwas dried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8bf5fe21c3ea4aca8666f6f2cfad7921
Source dataset
uspto-grants-2011_04
Patent number
US07932242B2

Reaction notes

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