Triethylamine → HCID 11433754, compound

HRID 2079490Notes

Reaction equation

HRID 2079490 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[C:20]([O:26][CH3:27])[C:4]=1[CH:5]=[CH:6][S:7]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:18][CH3:19])=[C:15]([OH:17])[CH:16]=1)(=[O:9])=[O:8].C(Br)(Br)(Br)Br.C(N(CC)CC)C.[P:40]([O-:57])([O:49][CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>C(#N)C>[P:40]([O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([O:49][CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)([O:17][C:15]1[CH:16]=[C:11]([CH2:10][S:7](/[CH:6]=[CH:5]/[C:4]2[C:20]([O:26][CH3:27])=[CH:21][C:22]([O:24][CH3:25])=[CH:23][C:3]=2[O:2][CH3:1])(=[O:9])=[O:8])[CH:12]=[CH:13][C:14]=1[O:18][CH3:19])=[O:57]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11205Carbon tetrabromideHCID 21904359DibenzylphosphiteHCID 727772735-((2,4,6-Trimethoxystyrylsulfonyl)methyl)-2-methoxy-phenol

Product 1

HCID 11433754HCID 11433754, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 5-((2,4,6-trimethoxystyrylsulfonyl)methyl)-2-methoxy-phenol (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. Dibenzyl 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-4b95d9a43a9c4e1da96ef3cd4ff440be
Source dataset
uspto-grants-2011_04
Patent number
US07932242B2

Reaction notes

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