4-bromo-1-tert-butyl-2-chlorobenzene

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was synthesized in analogy to 4-cyclopropyl benzaldehyde (described in example S53) using 4-bromo-1-tert-butyl-2-chloro-benzene (200 mg, 0.81 mmol), nBuLi (0.66 ml, 1.6M solution in hexane, 1.05 mmol) and DMF (251 μl, 3.23 mmol). The isolated residue was purified by flash column chromatography (1:9 ether:pentane) to give 4-tert-butyl-3-chloro-benzaldehyde (130 mg, 82%) as a colorless liquid. 1H NMR (CDCl3, 300 MHz): δ 9.94 (s, 1H), 7.85 (d, J=2 Hz, 1H), 7.70 (dd, J=2 and 8 Hz, 1H), 7.60 (d, J=8.0 Hz, 1H), 1.51 (s, 9H). The isolated residue was purified by flash column chromatography (1:9 ether:pentane)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was synthesized in analogy to 4-cyclopropyl benzaldehyde (described in example S53) using 4-bromo-1-tert-butyl-2-chloro-benzene (200 mg, 0.81 mmol), nBuLi (0.66 ml, 1.6M solution in hexane, 1.05 mmol) and DMF (251 μl, 3.23 mmol). The isolated residue was purified by flash column chromatography (1:9 ether:pentane) to give 4-tert-butyl-3-chloro-benzaldehyde (130 mg, 82%) as a colorless liquid. 1H NMR (CDCl3, 300 MHz): δ 9.94 (s, 1H), 7.85 (d, J=2 Hz, 1H), 7.70 (dd, J=2 and 8 Hz, 1H), 7.60 (d, J=8.0 Hz, 1H), 1.51 (s, 9H). The isolated residue was purified by flash column chromatography (1:9 ether:pentane)