Acetonitrile → HCID 86660546, compound

HRID 333112

Reaction equation

HRID 333112 reaction equation
[C:1]([O:6]C(=O)C(C)=C)(=[O:5])[C:2]([CH3:4])=[CH2:3].C(#N)C.[Br:15][C:16]([F:26])([F:25])[C:17]([F:24])([F:23])[CH2:18][CH2:19][CH2:20][CH2:21]O.C(N(CC)CC)C>O>[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[Br:15][C:16]([F:25])([F:26])[C:17]([F:23])([F:24])[CH2:18][CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 12974Methacrylic anhydrideHCID 232369226-Bromo-5,5,6,6-tetrafluorohexan-1-ol

Product 1

HCID 86660546HCID 86660546, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 300 mL reactor was charged under nitrogen with 18.2 g (119 mmol/1.5 equivalents) of methacrylic anhydride and 150 mL of acetonitrile, followed by putting it in an ice bath. 20.0 g (79.0 mmol/1.0 equivalent) of 6-bromo-5,5,6,6-tetrafluorohexan-1-ol was added thereto, followed by adding dropwise of 12.0 g (119 mmol/1.5 equivalents) of triethylamine. After the dropping, stirring was conducted at 60 degrees for 10 hours. Then, 100 mL of water was added, and extraction was conducted two times with 200 mL of diisopropyl ether. The obtained organic layer was washed further with diluted hydrochloric acid, sodium bicarbonate water and brine, followed by removing water by sodium sulfate and conducting filtration. Then, isopropyl ether was distilled out, thereby obtaining 23.8 g of the target 6-bromo-5,5,6,6-tetrafluorohexane methacrylate. Upon this, purity was 96%, and yield was 90%.

Workup

  1. extractionextraction
  2. washThe obtained organic layer was washed further with diluted hydrochloric acid, sodium bicarbonate water and brine
  3. customby removing water by sodium sulfate
  4. filtrationfiltration
  5. distillationThen, isopropyl ether was distilled out

Sources & evidence

ORD record
ord-1b990a540b2c470e917e76b793280537
Source dataset
uspto-grants-2014_11
Patent number
US08877960B2

Linked notes

Loading…