Allyl bromide → HCID 131732250, compound

HRID 1424544Notes

Reaction equation

HRID 1424544 reaction equation
[Br-:1].[C:2]1([CH2:28][N+:29]2([CH2:41][C:42]3C=CC=C[CH:43]=3)[CH:34]=[CH:33][C:32]([C:35]3[CH:40]=[CH:39][NH+:38]=[CH:37][CH:36]=3)=[CH:31][CH2:30]2)[CH:7]=[CH:6][C:5]([CH2:8][N+:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][N+:18]([CH2:21][C:22]4C=CC=C[CH:23]=4)=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[Br-].[Br-].[Br-].C([Br:54])C=C>>[Br-:54].[C:2]1([CH2:28][N+:29]2([CH2:41][CH:42]=[CH2:43])[CH:30]=[CH:31][C:32]([C:35]3[CH:36]=[CH:37][NH+:38]=[CH:39][CH:40]=3)=[CH:33][CH2:34]2)[CH:7]=[CH:6][C:5]([CH2:8][N+:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:16]=[CH:17][N+:18]([CH2:21][CH:22]=[CH2:23])=[CH:19][CH:20]=3)=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[Br-:1].[Br-:54].[Br-:54]

Participants

3

Reactant 2

HCID 7841Allyl bromideHCID 131732252HCID 131732252, compound

Product 1

HCID 131732250HCID 131732250, compound

Procedure

Compound 15 was synthesized as described above for compound 14, reflux time 3 h. Allyl bromide (1.97 g, 16.28 mmol), compound 4 (1.0 g, 1.42 mmol). The target compound was isolated as a bright yellow solid. Yield: 0.48 g, 42%. 1H NMR (D2O, 400 MHz): δ (ppm) 9.21-9.23 (4H, d), 9.14-9.16 (4H, d), 8.601 (8H, m), 7.68 (4H, s), 6.19-6.26 (2H, m), 6.03 (4H, s), 5.57-5.67 (2H, quad), 5.37-5.39 (2H, d). 13C NMR (D2O, 100 MHz): δ (ppm) 153.48, 153.04, 148.70, 148.66, 148.65, 148.63, 148.52, 148.46, 148.38, 136.95, 133.21, 132.33, 130.13, 129.89, 126.60, 67.01, 66.54.

Workup

  1. temperaturereflux time 3 h
  2. customThe target compound was isolated as a bright yellow solid

Sources & evidence

ORD record
ord-ee210329162743e78321fdd97246798b
Source dataset
uspto-grants-2015_01
Patent number
US08927727B2

Reaction notes

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