Diethyl Ether → HCID 86725159, compound

HRID 1779141Notes

Reaction equation

HRID 1779141 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:7](=[CH:8][CH:9]=1)[C:6](=[O:10])[CH2:5]2.[F:11][C:12]([F:26])([F:25])[C:13]1[CH:14]=[C:15]([Mg]Br)[CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:18]=1.[CH2:27](OCC)C>>[Br:1][C:2]1[CH:3]=[C:4]2[C:7](=[CH:8][CH:9]=1)[C:6]([CH2:27][C:15]1[CH:14]=[C:13]([C:12]([F:26])([F:25])[F:11])[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=1)([OH:10])[CH2:5]2

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 15547951407610-92-8HCID 178506227HCID 178506227, compound

Product 1

HCID 86725159HCID 86725159, compoundYield 76%

Procedure

Using 3-bromobicyclo[4.2.0]octa-1,3,5-triene-7-one (3) (2.0 g, 0.015 mol), diethyl ether (20 ml), 3,5-bis(trifluoromethyl)phenyl magnesium bromide (3M in diethyl ether, 3.8 ml, 11.7 mmol) afforded 3-Bromo-7-(3′,5′-bis(trifluoromethyl)benzyl)-bicyclo[4.2.0]octa-1,3,5-triene-7-ol (4b) (3.17 g, GC-MS: M+=410, M−=412, 76% yield, isolated as a mixture of isomers).

Sources & evidence

ORD record
ord-6134114f59d24097b7fdf8bc0e638aac
Source dataset
uspto-grants-2016_02
Patent number
US09269927B2

Reaction notes

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