N-bromobutanimide → 6-Bromo-5-oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

HRID 470585Notes

Reaction equation

[O:1]=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([C:12]#[N:13])[CH:5]=[CH:4][C:3]1=2.[Br:14]N1C(=O)CCC1=O.O.CC1C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[Br:14][CH:11]1[CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([C:12]#[N:13])[CH:5]=[CH:4][C:3]=2[C:2]1=[O:1]

Participants

Conditions

Temperature: 60 °C

Procedure

5-Oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (1.0 g, 5.8 mmol), 1-bromopyrrolidine-2,5-dione (1.04 g, 5.8 mmol) and 4-methylbenzenesulfonic acid hydrate (0.111 g, 0.58 mmol) were ground in a porcelain mortar. The resulting powder was placed in a vial, and heated at 60° C. for 12 mins. The mixture became a muddy liquid at 60° C. After cooling to room temperature, the mixture was dissolved in CH2Cl2 (80 mL). The solution was washed with saturated NaHCO3, water, brine, and dried (MgSO4). Solvent was evaporated off to give racemic 6-bromo-5-oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (1.25 g, 5.0 mmol, 86% yield) as a yellow solid: LCMS=249.98 [M+H]+.

Workup

customat 60° C
temperatureAfter cooling to room temperature
washThe solution was washed with saturated NaHCO3, water, brine
dry with materialdried (MgSO4)
customSolvent was evaporated off

Sources & evidence

ORD record: ord-945c40ded3e142519568da8e0e42fc19
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629282B2

Reaction notes

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