Allyl bromide → HCID 59804945, compound

HRID 604848Notes

Reaction equation

HRID 604848 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]([P:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:9]=[CH:10][CH:11]=2)=[N:2]1.[H-].[Na+].[H][H].[CH2:29](Br)[CH:30]=[CH2:31]>C1COCC1>[CH2:31]([N:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]([P:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:9]=[CH:10][CH:11]=2)=[N:2]1)[CH:30]=[CH2:29]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 178418361HCID 178418361, compoundHCID 178420540HCID 178420540, compound

Product 1

HCID 59804945HCID 59804945, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

25 mmol of 5 are dissolved in 50 ml of THF and mixed with 25 mmol of NaH. After the termination of the evolution of hydrogen, 25 mmol of allyl bromide are added and the mixture is refluxed for 4 h. After cooling to room temperature, it is filtered off from the NaBr precipitation and the solvent is removed in a vacuum. A colorless oil remains. Yield: 98%. 1H NMR (400.1 MHz, 25° C., DMSO-d6): δ 7.80-7.25 (m, 14H, ar H, 5pz-H), 7.06 (t, 1H, 3JHH=6.6 Hz, 5-H), 6.63 (d, 1H, 3JHH=2.4 Hz, 4pz-H), 6.07-5.96 (m, 1H, —CH═CH2), 5.20-5.11 (m, 2H, —CH═CH2), 4.75 (d, 2H, 3JHH=5.7 Hz, —CH2CH═). 13C{1H} NMR (100.6 MHz, 25° C., DMSO-d6): δ 150.5 (C-3pz), 139.4 (C-5pz), 137.6 (d, 1JPC=12.0 Hz, C-1), 134.7 (—CH═CH2), 134.1 (d, 2JPC=19.4 Hz, C-o), 132.9 (d, 3JPC=2.8 Hz, C-3), 132.8 (d, 2JPC=14.8 Hz, C-6), 132.4 (d, 1JPC=9.2 Hz, C-1), 130.9 (d, 2JPC=25.0 Hz, C-2), 130.0 (d, 3JPC=4.6 Hz, C-5), 129.8 (s, C-p), 129.6 (d, 3JPC=6.5 Hz, C-m), 126.7 (s, C-4), 118.7 (—CH═CH2), 103.6 (C-4pz) 54.7 (—CH2CH═). 31P{1H} NMR (162.0 MHz, 25° C., DMSO-d6): δ 4.90.

Workup

  1. temperaturethe mixture is refluxed for 4 h
  2. filtrationit is filtered off from the NaBr precipitation
  3. customthe solvent is removed in a vacuum

Sources & evidence

ORD record
ord-f2063b88fbec46e2a8c4046e708fbe75
Source dataset
uspto-grants-2011_03
Patent number
US07910744B2

Reaction notes

Loading…