Ethyl 4-bromocinnamate → HCID 86709742, compound

HRID 2174608Notes

Reaction equation

[I-].[CH:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([CH3:4])[CH3:3].[Br:24][C:25]1[CH:37]=[CH:36][C:28]([CH:29]=[CH:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:27][CH:26]=1>>[Br:24][C:25]1[CH:26]=[CH:27][C:28]([C@H:29]2[C@H:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:2]2([CH3:4])[CH3:3])=[CH:36][CH:37]=1

Participants

Reactant 2

HCID 141107Ethyl 4-bromocinnamate

HCID 2723783Isopropyltriphenylphosphonium iodide

Product 1

HCID 86709742HCID 86709742, compoundYield 54%

Procedure

Isopropyltriphenylphosphonium iodide (8.65 g, 20.0 mmol) and ethyl 4-bromo-cinnamate (5.10 g, 20.0 mmol) were reacted as described under General Procedure B to furnish the title compound (3.21 g, 54%) as a colourless oil. 1H NMR (300 MHz, CDCl3) δ 7.40 (d, J=8.3 Hz, 2H), 7.03 (d, J=8.3 Hz, 2H), 4.18 (q, J=7.1 Hz, 2H), 2.62 (d, J=5.5 Hz, 1H), 1.91 (d, J=5.5 Hz, 1H), 1.36 (s, 3H), 1.30 (t, J=7.1 Hz, 3H), 0.91 (s, 3H).

Sources & evidence

ORD record: ord-d303f6bcc8af48b9ad1f19b176ecc6d3
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09062013B2

Reaction notes

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