2-(2-Bromo-1,1,2,3,3,3-hexafluoropropanoxy)-1,3-dichlorobenzene → 7-Chloro-2,2,3-trifluoro-3-trifluoromethyl-2,3-dihydrobenzofuran

HRID 980251Notes

Reaction equation

HRID 980251 reaction equation
Br[C:2]([F:19])([C:15]([F:18])([F:17])[F:16])[C:3]([F:14])([F:13])[O:4][C:5]1[C:10](Cl)=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:12]>CS(C)=O.[Cu].C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:12][C:6]1[C:5]2[O:4][C:3]([F:14])([F:13])[C:2]([F:19])([C:15]([F:18])([F:17])[F:16])[C:10]=2[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 1

HCID 202224142-(2-Bromo-1,1,2,3,3,3-hexafluoropropanoxy)-1,3-dichlorobenzene

Product 1

HCID 202224127-Chloro-2,2,3-trifluoro-3-trifluoromethyl-2,3-dihydrobenzofuranYield 47.1%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 178419050HCID 178419050, compoundCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

In a manner similar to Step C of Example 2, the reaction of 12.8 g (0.033 mole) 2-(2-bromo-1,1,2,3,3,3-hexafluoropropanoxy)-1,3-dichlorobenzene, 10.4 g (0.16 mole) activated copper powder, and 2.3 g (0.0033 mole) bis(triphenylphosphine)palladium II chloride in 225 ml of dimethyl sulfoxide produced 4.3 g of 7-chloro-2,2,3-trifluro-3-trifluoromethyl-2,3-dihydrobenzofuran as an oil. The nmr spectrum was consistent with the proposed structure.

Sources & evidence

ORD record
ord-6468748fa62a47eba47be785cde6a05a
Source dataset
uspto-grants-1987_01
Patent number
US04636523

Reaction notes

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