Trifluoroacetic acid → HCID 71187127, compound

HRID 1779142Notes

Reaction equation

HRID 1779142 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:7](=[CH:8][CH:9]=1)[C:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(O)[CH2:5]2.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>CCCCCC>[Br:1][C:2]1[CH:3]=[C:4]2[C:7](=[CH:8][CH:9]=1)[CH:6]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH2:5]2

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 71187130HCID 71187130, compound

Product 1

HCID 71187127HCID 71187127, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Using 3-bromo-7-phenyl-bicyclo[4.2.0]octa-1,3,5-triene-7-ol (4a) (2.1 g, 7.6 mmol), hexane (10 ml), triethylsilane (1.3 g, 11.5 mmol), trifluoro acetic acid (4.3 g, 38.2 mmol) afforded 3-Bromo-7-phenyl-bicyclo[4.2.0]octa-1,3,5-triene (5a) as a pale yellow oil (1.5 g, GC-MS: M+=258, M−=260, 76% yield, isolated as a mixture of isomers).

Sources & evidence

ORD record
ord-0fcce28325904a5a89363db530d55d9f
Source dataset
uspto-grants-2016_02
Patent number
US09269927B2

Reaction notes

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