3'-Bromoacetophenone → HCID 60795076, compound

HRID 1668741Notes

Reaction equation

HRID 1668741 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([Mg]Br)[CH:5]=[CH:6][CH:7]=1.[CH3:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=1)=[O:12]>>[Br:19][C:15]1[CH:14]=[C:13]([C:11]([C:6]2[CH:7]=[C:2]([CH3:1])[CH:3]=[CH:4][CH:5]=2)([OH:12])[CH3:10])[CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 165023'-BromoacetophenoneHCID 178425413HCID 178425413, compound

Product 1

HCID 60795076HCID 60795076, compound

Procedure

In an analogous reaction sequence to that described for Building Block C, the reaction of 3-methyl phenylmagnesium bromide with 3-bromoacetophenone yielded the 1-(3-bromo-phenyl)-1-m-tolyl-ethanol which was used as crude material in the following elimination reaction with a catalytic amount of p-toluenesulfonic acid to yield the title compound (yield: 66% of theory) as a colourless oil. TLC: Rf: 0.83 (silica gel; heptane:ethyl acetate=4:1, UV, 254 nm).

Sources & evidence

ORD record
ord-82d1143cca7048d79aeb7de18b0bf2d4
Source dataset
uspto-grants-2011_08
Patent number
US07989449B2

Reaction notes

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