Bromoethene → HCID 57835887, compound

HRID 922200Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:34]=[CH:33][C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH:15]([CH2:29][N+:30]([O-:32])=O)[CH2:16][C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)=[O:18])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[CH:35](Br)=[CH2:36].C1(N=C=O)C=CC(N=C=O)=CC=1>C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:34]=[CH:33][C:6]([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]([CH:15]([C:29]3[CH:36]=[CH:35][O:32][N:30]=3)[CH2:16][C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)=[O:18])=[CH:13][CH:14]=2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a 50 mL RB flask fitted with magnetic stirrer was charged with 3 mL of triethyl amine. To this, added 4-methoxybenzyl 3-{4-[(4-methoxybenzyl)oxy]phenyl}-4-nitrobutanoate (0.25 g, 0.537 mmol) and followed by addition of vinyl bromide (4 ml), 1,4-phenylene diisocyanate (0.3 g, 1.87 mmol), refluxed at 85° C. for 8 h. The RM was cooled to RT, solid was precipitated. The solid was removed by filtration and the filtrate was evaporated under reduced pressure. The product obtained as a brown color gummy material (0.1 g, yield: 40.2%). 1H NMR (300 MHz, CDCl3): δ 8.17-8.18 (d, 1H), 7.25-7.28 (d, 2H), 7.05-7.11 (t, 4H), 6.75-6.85 (m, 6H), 5.97-5.98 (d, 1H), 4.92 (s, 2H), 4.86 (s, 2H), 4.46-4.52 (t, 1H), 3.73 (s, 3H), 3.72 (s, 3H), 3.18-3.26 (q, 1H), 2.85-2.93 (q, 1H).

Workup

customTo a 50 mL RB flask fitted with magnetic stirrer
temperatureThe RM was cooled to RT
customsolid was precipitated
customThe solid was removed by filtration
customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record: ord-20d065a0d3e04c70a3d9092c64a75c46
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278915B2

Reaction notes

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