Cesium carbonate → 6'-Bromospiro[cyclohexane-1,2'-indene]-1',4(3'H)-dione

HRID 473004Notes

Reaction equation

[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3([CH2:16][CH2:15][C:14](F)(F)[CH2:13][CH2:12]3)[C:8]2=[O:11])=[CH:4][CH:3]=1.C([O-])([O-])=[O:20].[Cs+].[Cs+]>>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3([CH2:16][CH2:15][C:14](=[O:20])[CH2:13][CH2:12]3)[C:8]2=[O:11])=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 10796Cesium carbonate

HCID 581972726'-bromo-4,4-difluorospiro[cyclohexane-1,2'-inden]-1'(3'H)-one

Product 1

HCID 581972056'-Bromospiro[cyclohexane-1,2'-indene]-1',4(3'H)-dioneYield 53%

Procedure

According to a similar synthesis of compound 344, compound 5 (100 mg, 0.26 mmol) was alkylated with compound 2 (159 mg, 1.04 mmol) in the presence of Cs2CO3 (339 mg, 1.04 mmol) to give compound 4 (73 mg, 53%).

Sources & evidence

ORD record: ord-f68003fd49a1426c99c19c639bdeb5be
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633212B2

Reaction notes

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