3-Bromo-4-fluorobenzaldehyde → HCID 23497510, compound

HRID 1837101Notes

Reaction equation

[NH2:1][C:2]1[N:3]([CH3:8])[O:4][C:5](=[O:7])[CH:6]=1.[C:9]([O:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])(=[O:11])[CH3:10].[Br:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][C:29]=1[F:30])[CH:25]=O>C(O)C>[C:9]([O:12][CH2:13][C:14]1[NH:1][C:2]2[N:3]([CH3:8])[O:4][C:5](=[O:7])[C:6]=2[CH:25]([C:24]2[CH:27]=[CH:28][C:29]([F:30])=[C:22]([Br:21])[CH:23]=2)[C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17])(=[O:11])[CH3:10]

Participants

Conditions

Temperature: 80 °C

Procedure

The product from Example 45A (0.17 g, 1.5 mmol), ethyl 4-(acetyloxy)butanoate (0.28 g, 1.5 mmol), prepared as described in (Husband, et al., Tetrahedron (1995) 51(3), 865), and 3-bromo-4-fluorobenzaldehyde (0.3 g, 1.5 mmol) in ethyl alcohol (4 mL) were heated at 80° C. for 24 hours in a sealed tube. The reaction mixture was evaporated under reduced pressure and the residue chromatographed on silica gel eluting with 5% ethanol/methylene chloride to provide the title compound (0.2 g). 1H NMR (300 MHz, DMSO-d6) δ 1.03 (t, 3H), 2.1 (s, 3H), 3.23 (s, 3H), 3.82 (q, 2H), 4.8 (s, 1H), 5.12 (q, 2H), 7.25 (m, 1H), 7.3 (t, 1H), 7.48 (dd, 1H), 10.2 (s, 1H); MS (ESI−) m/z 467 (M−H)−.

Workup

customThe reaction mixture was evaporated under reduced pressure
customthe residue chromatographed on silica gel eluting with 5% ethanol/methylene chloride

Sources & evidence

ORD record: ord-cf3d7c46f3674cc884103e3e4d8d3aba
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06780872B2

Reaction notes

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