Compound I

4-(2-(5-(3,5-bis(trifluoromethyl)phenyl)-2-methylthiophen-3-yl)cyclopent-1-en-1-yl)phenol

From: Light-driven molecular trap enables bidirectional manipulation of dynamic covalent systems

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Compound data: 1H NMR

Compound data: 13C NMR

Compound data: 19F NMR

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

Under an argon atmosphere, anisole 4 (0.98 g, 2.0 mmol, 1.0 eq.) was dissolved in 100 mL of dry dichloromethane, cooled to 0 °C, and treated with a 1M dichloromethane solution of boron tribromide (10.0 mL, 10.2 mmol, 5.0 eq.). After stirring for three hours at room temperature, the reaction mixture was quenched with ice water and diluted with dichloromethane. The organic phase was dried over magnesium sulfate, filtered over a pad of silica gel, and purified by flash column chromatography (SiO2; cyclohexane/ethyl acetate 75:25), providing the product (0.7 g, 76%) as a colorless solid. For photochemical experiments, the compound was additionally purified by recycling GPC. 1H NMR (500 MHz, CD2Cl2, 25 °C): δ = 7.96 (s, 2H), 7.74 (s, 1H), 7.26 (s, 1H), 7.19–7.00 (m, 2H), 6.80–6.57 (m, 2H), 4.82 (s, 1H), 2.89 (tt, 3,4J(H,H) = 7.5, 2.2 Hz, 2H), 2.79 (tt, 3,4J(H,H) = 7.5, 2.2 Hz, 2H), 2.06 (p, 3J(H,H) = 7.4 Hz, 2H), 2.02 (s, 3H) ppm. 13C{1H} NMR (126 MHz, CD2Cl2, 25 °C): δ = 154.91 (s), 139.07 (s), 138.61 (s), 137.23 (s), 137.23 (s), 137.16 (s), 132.48 (q, 2J(C,F) = 33.2 Hz), 131.77 (s), 131.12 (s), 129.08 (s), 127.21 (s), 125.56 (q, 3J(C,F) = 3.8 Hz), 123.96 (q, 1J(C,F) = 272.6 Hz), 120.60 (hept, 3J(C,F) = 4.0 Hz), 115.39 (s), 40.32 (s), 37.69 (s), 22.9 (s), 14.52 (s) ppm. 19F NMR (471 MHz, CD2Cl2, 25 °C): δ = –63.66 (s, 6F) ppm. MS (ESI+): m/z calculated for C24H19F6OS [M+H]+: 469.106, found: 469.104.