Triethylamine → HCID 18402852, compound

HRID 1017157Notes

Reaction equation

[CH:1]1[C:9]2[CH:8]=[C:7]3[CH:10]=[CH:11][CH:12]=[CH:13][C:6]3=[CH:5][C:4]=2[CH2:3][CH:2]=1.Br[C:15]1[CH:20]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:18]=[C:17]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:16]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:25]([C:17]1[CH:16]=[C:15]([C:2]2[CH2:3][C:4]3[CH:5]=[C:6]4[CH:13]=[CH:12][CH:11]=[CH:10][C:7]4=[CH:8][C:9]=3[CH:1]=2)[CH:20]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:18]=1)([CH3:28])([CH3:27])[CH3:26]

Participants

Conditions

Temperature: 60 °C

Procedure

Benz[f]indene (10.8 g, 0.065 mole) was dissolved in 100 mL of dimethylformamide. 1-Bromo-3,5-di-t-butylbenzene (14 g, 0.052 mole) was added along with palladium acetate (0.3 g), tri-o-tolylphosphine (0.8 g), and triethyl amine (11.0 g). The solution was heated to 60° C. for 3 days. The solution was cooled and washed with 1 N HCl and by saturated sodium bicarbonate. The product was found to be difficult to separate from the residual tri-o-tolylphosphine. After purifying by passing through silica with hexanes three times, and recrystallization from ethanol, followed by three recrystallizations from hexanes, it yielded 5.8 g of 2-(3,5-di-t-butylphenyl)benz[f]indene (26% yield). 1HNMR (CDCl3, 300 MHz δ7.95-7.77 (m, 4H); 7.52-7.37 (m, 5H); 7.23 (s, 1H); 3.99 (s, 2H); 1.43 (s, 18H).

Workup

temperatureThe solution was cooled
washwashed with 1 N HCl and by saturated sodium bicarbonate
customto separate from the residual tri-o-tolylphosphine
customAfter purifying
customwith hexanes three times, and recrystallization from ethanol
customfollowed by three recrystallizations from hexanes, it

Sources & evidence

ORD record: ord-a93bcc50715446f597159d5de8fbfa01
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06479424B1

Reaction notes

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