Bromoethene → HCID 57835887, compound

HRID 731208Notes

Reaction equation

HRID 731208 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

5

Reactant 3

HCID 11641BromoetheneHCID 610091,4-DiisocyanatobenzeneHCID 57835770HCID 57835770, compound

Product 1

HCID 57835887HCID 57835887, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

Triethylamine (1 mL) was added to a mixture of 76.3 (1.89 g, 4.1 mmol), vinyl bromide (32.5 mL, 1.0 M solution in THF) and 1,4-phenylene diisocyanate (2.3 g, 14.35 mmol). The mixture was stirred at 80° C. for 8 hours. After cooling, the solid was removed from the mixture by filtration, and the filtrate was concentrated and purified by flash chromatography to give 76.4 (3 g). MS ESI (pos.) m/e: 474 (M+H). 1HNMR (CDCl3) δ 8.28 (d, 1H), 7.37 (d, 2H), 7.18 (m, 4H), 6.92 (m, 6H), 6.07 (d, 1H), 5.02 (s, 2H), 4.97 (s, 2H), 4.59 (t, 1H), 3.84 (s, 3H), 3.82 (s, 3H), 3.33 (dd, 1H), 3.00 (dd, 1H).

Workup

  1. temperatureAfter cooling
  2. customthe solid was removed from the mixture by filtration
  3. concentrationthe filtrate was concentrated
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-25829313d7e74160b154d62195add689
Source dataset
uspto-grants-2009_09
Patent number
US07582803B2

Reaction notes

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