p-Xylyl bromide → HCID 57658810, compound

HRID 910054Notes

Reaction equation

HRID 910054 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.C([O:12][C:13](=[O:31])[CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][C:17]=1/[CH:23]=[C:24]1/[C:25](=[O:30])[NH:26][C:27](=[O:29])[S:28]/1)C>>[Br:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][CH2:14][C:13]([OH:31])=[O:12])=[C:17]([CH2:23][CH:24]2[S:28][C:27](=[O:29])[N:26]([CH2:6][C:5]3[CH:8]=[CH:9][C:2]([CH3:1])=[CH:3][CH:4]=3)[C:25]2=[O:30])[CH:18]=1

Participants

3

Reactant 2

HCID 7721p-Xylyl bromideHCID 16634246HCID 16634246, compound

Product 1

HCID 57658810HCID 57658810, compound

Procedure

Prepared from 4-methylbenzylbromide and 4-bromo-2-[2,4-dioxothiazolidin-(5Z)-ylidenemethyl]phenoxyacetic acid ethyl ester according to GP13, GP14 and GP16 (yield: 14 mg, 21%): LC/MS (an10p8): Rt 2.5 min, m/z 462 [M−H]−. 1H NMR (DMSO-d6): δ 2.98-3.07 (m, 1H), 3.53-3.59 (m, 1H), 4.63 (s, 2H), 4.74 (s, 2H), 5.07-5.13 (m, 1H), 6.89-6.91 (m, 1H), 7.11-7.16 (m, 4H), 7.38-7.43 (m, 2H), 13.11 (br s, 1H).

Sources & evidence

ORD record
ord-2ecfadbe0a084e0cb7a4c33c8713ecf5
Source dataset
uspto-grants-2011_09
Patent number
US08022063B2

Reaction notes

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