Hydrochloric Acid → HCID 86606152, compound

HRID 1593716Notes

Reaction equation

HRID 1593716 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=3)[C:5]([CH2:20][CH2:21][CH2:22][OH:23])([CH2:16][CH2:17][CH2:18][OH:19])[C:4]=2[CH:3]=1.C(N(C(C)C)CC)(C)C.[C:33](Cl)(=[O:36])[CH:34]=[CH2:35].Cl.[O:39]1C[CH2:42][CH2:41][CH2:40]1>C(OCC)(=O)C>[C:33]([O:23][CH2:22][CH2:21][CH2:20][C:5]1([CH2:16][CH2:17][CH2:18][O:19][C:40](=[O:39])[CH:41]=[CH2:42])[C:4]2[CH:3]=[C:2]([Br:1])[CH:14]=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=2)(=[O:36])[CH:34]=[CH2:35]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 58473603HCID 58473603, compound

Product 1

HCID 86606152HCID 86606152, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
10 °C

Procedure

A solution containing 15 grams of 3-[2,7-Dibromo-9-(3-hydroxypropyl)-9H-fluorene-9-yl]-propane-1-ol and 18.7 grams of diisopropylethylamine in 150 ml of tetrahydrofuran was cooled to 10° C., and to it was slowly added a solution of 7.7 grams of acryloyl chloride in 18 ml of tetrahydrofuran. The temperature was maintained at 10° C. during the addition. After stirring at 10° C. for one hour the mixture was poured into a mixture containing 100 ml of 2% aqueous HCl and 100 ml of ethyl acetate. The organic phase was separated and dried over anhydrous sodium sulfate. The solvent was removed and the residue purified by column chromatography on silica gel eluted with 15% ethyl acetate in hexane to give 8.5 grams of acrylic acid 3-[9-(acryloyloxy-propyl)-2,7-dibromo-9H-fluoren-9-yl]-propyl ester. This product was verified by NMR analysis to be present and pure.

Workup

  1. temperatureThe temperature was maintained at 10° C. during the addition
  2. additionwas poured into a mixture
  3. customThe organic phase was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed
  6. customthe residue purified by column chromatography on silica gel
  7. washeluted with 15% ethyl acetate in hexane

Sources & evidence

ORD record
ord-cda7db517289452490d50dd182756e05
Source dataset
uspto-grants-2007_11
Patent number
US07297810B2

Reaction notes

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