6-Bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene → 3-Nitro-4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ylamino)benzonitrile

HRID 2233069Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:13])([CH3:12])[CH2:7][CH2:6][C:5]2([CH3:15])[CH3:14].[NH2:16][C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][C:18]=1[N+:25]([O-:27])=[O:26].CC([O-])(C)C.[Na+].C(PC1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>C1COCC1>[N+:25]([C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][C:17]=1[NH:16][C:2]1[CH:11]=[CH:10][C:9]2[C:8]([CH3:13])([CH3:12])[CH2:7][CH2:6][C:5]([CH3:15])([CH3:14])[C:4]=2[CH:3]=1)[C:21]#[N:22])([O-:27])=[O:26]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (61.3 mmol) and 4-amino-3-nitrobenzonitrile (61.3 mmol) in THF (150 mL) are added NaOtBu (67.4 mmol), 2-(t-butylphosphino)biphenyl (6.13 mmol), and Pd2(bda)3 (3.06 mmol) at room temperature. The reaction mixture is heated at 80° C. for 2 h. After cooling, the mixture is filtered through Celite. The filtrate is diluted with H2O and extracted with EtOAc. The organic layer is dried over MgSO4 and evaporated in vacuo. The resulting solid is washed with a mixture of hexane and EtOAc (8:1) to give (30).

Workup

temperatureAfter cooling
filtrationthe mixture is filtered through Celite
additionThe filtrate is diluted with H2O
extractionextracted with EtOAc
dry with materialThe organic layer is dried over MgSO4
customevaporated in vacuo
washThe resulting solid is washed with a mixture of hexane and EtOAc (8:1)

Sources & evidence

ORD record: ord-31eec4959383420ebb80dd3b370100e9
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709470B2

Reaction notes

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