Trifluoromethanesulfonic acid → 6-bromo-3-methyl-3,4-dihydronaphthalen-1(2H)-one

HRID 514052Notes

Reaction equation

FC(F)(F)S(O)(=O)=O.[Br:9][C:10]1[CH:11]=[C:12]([CH2:16][CH:17]([CH3:22])[CH2:18][C:19]([OH:21])=O)[CH:13]=[CH:14][CH:15]=1>C(Cl)Cl.C(Cl)(Cl)Cl>[Br:9][C:10]1[CH:11]=[C:12]2[C:13](=[CH:14][CH:15]=1)[C:19](=[O:21])[CH2:18][CH:17]([CH3:22])[CH2:16]2

Participants

Conditions

Temperature: 0 °C

Procedure

A flask was charged with trifluoromethane sulfonic acid (450 g, 3 mol) and cooled to 0° C. with an ice-water bath. 4-(3-bromophenyl)-3-methylbutanoic acid, prepared in a similar manner as described in Example 32 (15.5 g, 60 mmol), was added as a solution in DCM (30 mL) slowly to produce a clear dark brown solution. After 15 min, the reaction was diluted with 500 mL of CHCl3 and poured slowly onto approximately 1 L of crushed ice. The resulting slurry was allowed to stir until the solution warms to room temperature and became biphasic. Following separation of layers, the aqueous layer was extracted with CHCl3. The combined organics were washed with brine and dried over anhydrous MgSO4 prior to concentration in vacuo. Purification via Isco column chromatography (50% DCM/hex isocratic) provided a quantitative yield of the named compound as a pale yellow amorphous solid. LCMS-ESI+ (m/z): [M]+ calcd for C11H11BrO: 239.11; found: 239.20.

Workup

customto produce a clear dark brown solution
customwarms to room temperature
customseparation of layers
extractionthe aqueous layer was extracted with CHCl3
washThe combined organics were washed with brine
dry with materialdried over anhydrous MgSO4
concentrationto concentration in vacuo
customPurification via Isco column chromatography (50% DCM/hex isocratic)

Sources & evidence

ORD record: ord-1d78bf7c376a4fdd86124431795d2d10
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102614B2

Reaction notes

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