Potassium Bromide → {4-[4-(4-Chloro-benzyloxy)-benzylsulfanyl]-2-methyl-phenoxy}-acetic Acid

HRID 1063708Notes

Reaction equation

C[O:2][C:3](=[O:30])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)=[CH:16][CH:15]=2)=[CH:8][C:7]=1[CH3:29].[K+].[Br-]>>[Cl:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][O:20][C:17]2[CH:16]=[CH:15][C:14]([CH2:13][S:12][C:9]3[CH:10]=[CH:11][C:6]([O:5][CH2:4][C:3]([OH:30])=[O:2])=[C:7]([CH3:29])[CH:8]=3)=[CH:19][CH:18]=2)=[CH:27][CH:26]=1

Participants

Reactant 2

HCID 253877Potassium Bromide

HCID 20827026HCID 20827026, compound

Product 1

HCID 22280026{4-[4-(4-Chloro-benzyloxy)-benzylsulfanyl]-2-methyl-phenoxy}-acetic Acid

Procedure

The title compound was prepared in the manner analogous to Example 1 using 58A. mp 164° C.; IR (KBr) cm−1: 3062, 1727, 1612, 1493, 1226, 1193; 400 MHz 1H NMR (DMSO-d6): δ 12.99 (br(s), 1H), 7.36-7.44 (m, 4H), 7.01-7.17 (m, 4H), 6.81-6.89 (m, 2H), 6.69 (d, 1H, J=8.5 Hz), 5.01 (s, 2H), 4.61 (s, 2H), 4.00 (s, 2H), 2.08 (s, 3H); MS m/z 427 (M−1). Anal. Calc'd for C23H21ClO4S: C, 64.40; H, 4.93. found: C, 64.43; H, 4.81.

Sources & evidence

ORD record: ord-44b813bf25ab40c8ab85f79f0485729e
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06964983B2

Reaction notes

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