Carbon tetrabromide → HCID 86751440, compound

Participants

Reaction Steps

To a mixture of zinc dust (4.10 g, 63 mmol) and triphenylphosphine (16.5 g, 63 mmol) in CH2Cl2 (100 ml) was added carbon tetrabromide (20.9 g, 63 mmol). After stirring for 5 h, cis-3-(4-fluorophenoxy)cyclopentanecarbaldehyde (4.00 g, 9.2 mmol) was added to the mixture and the whole stirred overnight at room temperature (Tetrahedron Lett., 1972, 3769). The reaction mixture was filtered through a short colummn of silica gel and the filtrate concentrated in vacuo to afford 6.12 g (85%) of title compound as a light yellow oil: 1H NMR δ7.06-6.93 (m, 2H), 6.85-6.73 (m, 2H), 6.45 (d, J=9.2 Hz, 1H), 4.75-4.68 (m, 1H), 2.91-2.76 (m, 1H), 2.44-2.30 (m, 1H), 2.08-1.55 (m, 5H).

Provenance & Evidence