Sodium Hydroxide → 7-Bromo-1,2,3,4-tetrahydronaphthalen-1-one

HRID 883598Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O)=[CH:4][CH:3]=1.[OH-].[Na+]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([CH2:8][CH2:9][CH2:10][C:11]2=[O:13])=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 2527324-(4-Bromophenyl)butyric Acid

Product 1

HCID 2527317-Bromo-1,2,3,4-tetrahydronaphthalen-1-oneYield 55%

Conditions

Temperature: 90 °C

Procedure

The product from Step B (97 g, 397 mmol) was added to polyphosphoric acid (580 g) and the resulting mixture was stirred at 90° C. for 10 minutes. After cooling to 0° C., 6 M NaOH (2 l) was added and the mixture was extracted with methyl tert-butyl ether. The organic extracts were dried over magnesium sulfate to give 7-bromo-3,4-dihydronaphthalen-1-one (49 g, 55%) after chromatography (6:1 to 4:1 heptane/ethyl acetate) and recrystallization from cyclohexane: 1H NMR (300 MHz, DMSO-d6) δ 7.91 (d, J=2.1 Hz, 1H), 7.71 (dd, J=8.1, 2.1 Hz, 1H), 7.34 (d, J=8.1 Hz, 1H), 2.90 (t, J=6.0 Hz, 2H), 2.61 (t, J=6.3 Hz, 2H), 1.99-2.07 (m, 2H).

Workup

temperatureAfter cooling to 0° C.
extractionthe mixture was extracted with methyl tert-butyl ether
dry with materialThe organic extracts were dried over magnesium sulfate

Sources & evidence

ORD record: ord-881b2a0ab9eb4013a09934bb04ed12a6
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236796B2

Reaction notes

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