HCID 67126180, compound → 7-Bromo-3-methyl-3,4-dihydronaphthalen-1(2H)-one

HRID 514053Notes

Reaction equation

HRID 514053 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([CH3:14])[CH2:10][C:11]([OH:13])=O)=[CH:4][CH:3]=1>OS(O)(=O)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([CH2:8][CH:9]([CH3:14])[CH2:10][C:11]2=[O:13])=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 67126180HCID 67126180, compound

Product 1

HCID 671261607-Bromo-3-methyl-3,4-dihydronaphthalen-1(2H)-oneYield 96%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
75 °C

Procedure

A solution of 4-(4-bromophenyl)-3-methylbutanoic acid, prepared in a similar manner as described in Example 32 (6.43 g, 25.0 mmol), in H2SO4 (25 mL) was stirred at 75° C. for 3 h. The mixture was slowly poured onto ice. The resulting slurry was extracted with EtOAc (2×100 mL). The combined organic layers were washed with brine, dried, filtered, and concentrated in vacuo. The crude material was purified by column chromatography (EtOAc/hexanes) to give 5.74 g (96%) of the title compound. 1H-NMR: 400 MHz, (CDCl3) δ: 8.10 (d, J=2 Hz, 1H), 7.54 (dd, J=8, 2 Hz, 1H), 7.11 (d, J=8 Hz, 1H), 2.91 (d, J=16 Hz), 2.71 (d, J=13 Hz), 2.58 (m, 1H), 2.28 (m, 2H), 1.12 (d, J=6 Hz, 3H).

Workup

  1. additionThe mixture was slowly poured onto ice
  2. extractionThe resulting slurry was extracted with EtOAc (2×100 mL)
  3. washThe combined organic layers were washed with brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by column chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-41fe9642453c4dc2bc4e0553d055b3f3
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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