1-(Bromomethyl)-4-chlorobenzene → HCID 57658757, compound

HRID 910053Notes

Reaction equation

HRID 910053 reaction equation
[Cl: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]([Cl:1])=[CH:3][CH:4]=3)[C:25]2=[O:30])[CH:18]=1

Participants

3

Reactant 2

HCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 16634246HCID 16634246, compound

Product 1

HCID 57658757HCID 57658757, compound

Procedure

Prepared from 4-chlorobenzylbromide and 4-bromo-2-[2,4-dioxothiazolidin-(5Z)-ylidenemethyl]phenoxyacetic acid ethyl ester according to GP13, GP14 and GP16 to give 50.4 mg (21% overall yield) of the title compound: LC/MS (an10p8): Rt 2.6 min, m/z 482 [M−H]−. 1H NMR (DMSO-d6): δ 3.05 (dd, J=13.8, 9.7 Hz, 1H), 3.57 (dd, J=13.8, 4.9 Hz, 1H), 5.11 (dd, J=9.7, 4.9 Hz, 1H), 4.67 (s, 2H), 4.75 (s, 2H), 6.91 (d, J=8.7, 1H), 7.25-7.28 (m, 2H), 7.37-7.42 (m, 4H), 13.15 (br. s, 1H).

Workup

  1. customto give

Sources & evidence

ORD record
ord-201f91706b3a44d68c9c5d5720b8ead0
Source dataset
uspto-grants-2011_09
Patent number
US08022063B2

Reaction notes

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