Potassium Bromide → {7-[4-(2,5-Dichloro-benzyloxy)-benzylsulfanyl]-indan-4-yloxy}-acetic acid

HRID 1063725Notes

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]=[C:29]([Cl:31])[CH:28]=[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]=[CH:28][C:29]([Cl:31])=[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 20827080{7-[4-(2,5-Dichloro-benzyloxy)-benzylsulfanyl]-indan-4-yloxy}-acetic acid methyl ester

Product 1

HCID 22280187{7-[4-(2,5-Dichloro-benzyloxy)-benzylsulfanyl]-indan-4-yloxy}-acetic acid

Procedure

The title compound was prepared in the manner analogous to Example 1 using 71A. mp 158-160° C.; IR (KBr) cm−1: 3070, 2573, 1747, 1716, 1236, 1106; 400 MHz 1H NMR (DMSO-d6): δ 12.95 (br(s), 1H), 7.57-7.62 (m, 1H) 7.47-7.53 (m, 1H), 7.38-7.45 (m, 1H), 7.08-7.16 (m, 2H), 7.04 (d, 1H, J=8.5 Hz), 6.85-6.92 (m, 2H), 6.56 (d, 1H, J=8.5 Hz), 5.06 (s, 2H), 4.61 (s, 2H), 3.94 (s, 2H), 2.75 (t, 2H, J=7.3 Hz), 2.67 (t, 2H, J=7.3 Hz), 1.89 (pentet, 2H); MS m/z 487 (M−1). Anal. Calc'd for C25H22Cl2O4S: C, 61.35; H, 4.53. found: C, 61.24; H, 4.43.

Sources & evidence

ORD record: ord-5be476fa98d045478261df3b92280718
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06964983B2

Reaction notes

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