Dimethylformamide → HCID 86761886, compound

Participants

Reaction Conditions

Reaction Steps

To a flame-dried 3-neck round-bottomed flask equipped with a mechanical stirrer and an addition funnel was added 2,7-dibromo-9,9-bis(3,7-dimethyloctyl)fluorene (Example 6; 79.3 g, 131.2 mmol) and THF (350 mL) by cannula. The solution was cooled to −78° C. and 2.5 M n-BuLi in hexane (52.5 mL, 131.2 mmol) was added by addition funnel over 15 min. After stirring for 30 min, N,N-dimethylformamide (DMF, 20.0 mL, 262 mmol) in THF (30 mL) was added dropwise, and the reaction mixture was allowed to warm to room temperature overnight. Toluene and water were added, and the organic phase was further washed with water, dried with MgSO4, and concentrated. The crude product was purified by column chromatography eluting with heptane to 20% toluene/heptane to give 54 g (75%). 1H NMR (400 MHz, CDCl3) δ: 10.06 (s, 1H), 7.88-7.79 (m, 3H), 7.63 (m, 1H), 7.51 (m, 2H), 1.41 (m, 2H), 1.20-0.93 (m, 12H), 0.92-0.75 (m, 14H), 0.66 (m, 6H), 0.60-0.30 (m, 4H). Mass Spec. m/z 552, 554 (M+). Anal. Calcd. for C34H49BrO: C, 73.76%; H, 8.92%; Br, 14.43%. Found: C, 73.80%; H, 8.86%; Br, 14.64%.

Provenance & Evidence