Potassium Bromide → {7-[4-(2,4-Dichloro-benzyloxy)-benzylsulfanyl]-indan-4-yloxy}-acetic acid

HRID 1063712Notes

Reaction equation

C[O:2][C:3](=[O:33])[CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:12]([S:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=3[Cl:32])=[CH:19][CH:18]=2)=[C:11]2[C:7]=1[CH2:8][CH2:9][CH2:10]2.[K+].[Br-]>>[Cl:32][C:26]1[CH:27]=[C:28]([Cl:31])[CH:29]=[CH:30][C:25]=1[CH2:24][O:23][C:20]1[CH:19]=[CH:18][C:17]([CH2:16][S:15][C:12]2[CH:13]=[CH:14][C:6]([O:5][CH2:4][C:3]([OH:33])=[O:2])=[C:7]3[C:11]=2[CH2:10][CH2:9][CH2:8]3)=[CH:22][CH:21]=1

Participants

Reactant 2

HCID 253877Potassium Bromide

HCID 20827078{7-[4-(2,4-Dichloro-benzyloxy)-benzylsulfanyl]-indan-4-yloxy}-acetic acid methyl ester

Product 1

HCID 22280129{7-[4-(2,4-Dichloro-benzyloxy)-benzylsulfanyl]-indan-4-yloxy}-acetic acid

Procedure

The title compound was prepared in the manner analogous to Example 1 using 62A. mp 149-150° C.; IR (KBr) cm−1: 3089, 1734, 1512, 1473, 1295, 1234; 400 MHz 1H NMR (DMSO-d6): δ 13.11 (br(s), 1H), 7.40-7.71 (m, 3H), 6.88-7.19 (m, 5H), 6.58 (d, 1H, J=8.5 Hz), 5.07 (s, 2H), 4.61 (s, 2H), 3.96 (s, 2H), 2.77 (t, 2H, t, J=7.4 Hz), 2.69 (t, 2H, J=7.4 Hz), 1.91 (pentet, 2H); MS m/z 487 (M−1). Anal. Calc'd for C25H22Cl2O4S: C, 61.35; H, 4.53. found: C, 60.95; H, 4.41.

Sources & evidence

ORD record: ord-0ae3078dfc99479f944daae6720c6002
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06964983B2

Reaction notes

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