Benzoyl chloride → 6-Bromo-5,5,6,6-tetrafluorohexane benzoate
Reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:10]1CCCC1.[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:8])(=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:15][C:16]([F:25])([F:26])[C:17]([F:23])([F:24])[CH2:18][CH2:19][CH2:20][CH3:21]Participants
Procedure
A 300 mL reactor was charged under nitrogen with 14.0 g (99.6 mmol/1.3 equivalents) of benzoyl chloride and 150 mL of tetrahydrofuran (a dehydrated product), following 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 24.4 g of the target 6-bromo-5,5,6,6-tetrafluorohexane benzoate. Upon this, purity was 95%, and yield was 82%.
Workup
- extractionextraction
- washThe obtained organic layer was washed further with diluted hydrochloric acid, sodium bicarbonate water and brine
- customby removing water by sodium sulfate
- filtrationfiltration
- distillationThen, isopropyl ether was distilled out
Sources & evidence
- ORD record
- ord-ee33bbdddfbb4b1088a1eed55b041008
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08877960B2
Reaction notes
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