(4-Bromo-3,5-dimethylphenyl)trimethylsilane → 4-(2,6-Dimethyl-4-(trimethylsilyl)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-one

HRID 237483Notes

Reaction equation

HRID 237483 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5](B2OC(C)(C)C(C)(C)O2)=[C:6]2[C:10]=1[C:9](=[O:11])[CH2:8][CH2:7]2.Br[C:22]1[C:27]([CH3:28])=[CH:26][C:25]([Si:29]([CH3:32])([CH3:31])[CH3:30])=[CH:24][C:23]=1[CH3:33]>>[CH3:28][C:27]1[CH:26]=[C:25]([Si:29]([CH3:30])([CH3:32])[CH3:31])[CH:24]=[C:23]([CH3:33])[C:22]=1[C:5]1[CH:4]=[CH:3][C:2]([F:1])=[C:10]2[C:6]=1[CH2:7][CH2:8][C:9]2=[O:11]

Participants

3

Reactant 2

HCID 86697146(4-Bromo-3,5-dimethylphenyl)trimethylsilaneHCID 866971487-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-1-one

Product 1

HCID 866971474-(2,6-Dimethyl-4-(trimethylsilyl)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-one

Procedure

The title compound is prepared from 7-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-1-one and (4-bromo-3,5-dimethylphenyl)trimethylsilane following a procedure analogous to that described in Step 5 of Intermediate 1. LC (method 8): tR=0.89 min; Mass spectrum (ESI+): m/z=327 [M+H]+.

Sources & evidence

ORD record
ord-87bf6dbcbfc94834885e4d1e7fb020a1
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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