Bromoacetyl bromide → HCID 178444135, compound

HRID 275573Notes

Reaction equation

[PH:1](=[O:4])([OH:3])[OH:2].[CH2:5]([C:7]([CH2:35][CH3:36])([CH:9]([OH:34])[C:10]1[N:14]=[CH:13][N:12]([C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:11]=1)[CH3:8])[CH3:6].[Br:37][CH2:38][C:39](Br)=[O:40]>>[PH:1](=[O:2])([OH:4])[OH:3].[CH2:35]([C:7]([CH2:5][CH3:6])([CH:9]([O:34][C:39](=[O:40])[CH2:38][Br:37])[C:10]1[N:14]=[CH:13][N:12]([C:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:11]=1)[CH3:8])[CH3:36]

Participants

Reactant 2

HCID 61147Bromoacetyl bromide

HCID 178444075HCID 178444075, compound

Product 1

HCID 178444135HCID 178444135, compoundYield 32.3%

Procedure

Diethyl 3-hydroxy-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (1.0 g, prepared as described in Example 24) was acylated with bromoacetyl bromide (0.50 g) in a manner similar to the acetylation described in Example 26. Diethyl 3(bromoacetoxy)-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (0.40 g) was isolated as a colourless gum. NMR (CDCl3): δ 1.3(6H,t), 1.7-1.9(2H,m), 2.3(2H,m), 3.8-3.95(2H,m), 4.1(4H,m), 6.0(1H,t), 7.1-7.3(15H,m), 7.9(1H,2xs). FAB M/S: MH+ 626,628. IR: 1746 cm-1 carbonyl.

Sources & evidence

ORD record: ord-5e1988a946fe4ef193131e238ebc1cc6
Source dataset: uspto-grants-1995_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05393732

Reaction notes

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