Trifluoroacetic acid → {4-[4-(4-Methoxy-benzyloxy)-benzylsulfanyl]-2-methyl-phenoxy}-acetic acid

HRID 1063684Notes

Reaction equation

HRID 1063684 reaction equation
C[O:2][C:3](=[O:31])[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]([O:28][CH3:29])=[CH:24][CH:23]=3)=[CH:16][CH:15]=2)=[CH:8][C:7]=1[CH3:30].C(O)(C(F)(F)F)=O.[K+].[Br-]>C(#N)C.O>[CH3:29][O:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:21][O:20][C:17]2[CH:18]=[CH:19][C:14]([CH2:13][S:12][C:9]3[CH:10]=[CH:11][C:6]([O:5][CH2:4][C:3]([OH:31])=[O:2])=[C:7]([CH3:30])[CH:8]=3)=[CH:15][CH:16]=2)=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 253877Potassium BromideHCID 20827029HCID 20827029, compound

Product 1

HCID 22280141{4-[4-(4-Methoxy-benzyloxy)-benzylsulfanyl]-2-methyl-phenoxy}-acetic acid

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

The title compound was prepared in the manner analogous to Example 1 using 33C. mp 150-152° C.; HPLC: area %=96.69, r.t.=2.93 min., γ=214 nm, mobile phase=acetonitrile/water with 0.10% TFA; IR (KBr) cm−1: 2929, 1728, 1707, 1513, 1491, 1225; 400 MHz 1H NMR (DMSO-d6): δ 12.98 (br(s), 1H), 7.27-7.34 (m, 2H), 7.02-7.16 (m, 4H), 6.81-6.91 (m, 4H), 6.69 (d, 1H, J=8.6 Hz), 4.91 (s, 2H), 4.61 (s, 2H), 3.99 (s, 2H), 3.69 (s, 3H), 2.08 (s, 3H); MS m/z 423 (M−1). Anal. Calc'd for C24H24O5S: C, 67.90; H, 5.70. found: C, 67.48; H, 5.59.

Sources & evidence

ORD record
ord-af5c904f8aea4e0990b2a2723061f5e6
Source dataset
uspto-grants-2005_11
Patent number
US06964983B2

Reaction notes

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