Potassium Bromide → {8-[4-(2,5-Dichloro-benzyloxy)-benzylsulfanyl]-chroman-5-yloxy}-acetic Acid

HRID 1063749Notes

Reaction equation

HRID 1063749 reaction equation
C[O:2][C:3](=[O:34])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([S:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]3[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=3[Cl:33])=[CH:20][CH:19]=2)=[C:12]2[C:7]=1[CH2:8][CH2:9][CH2:10][O:11]2.[K+].[Br-]>>[Cl:33][C:27]1[CH:28]=[CH:29][C:30]([Cl:32])=[CH:31][C:26]=1[CH2:25][O:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][S:16][C:13]2[CH:14]=[CH:15][C:6]([O:5][CH2:4][C:3]([OH:34])=[O:2])=[C:7]3[C:12]=2[O:11][CH2:10][CH2:9][CH2:8]3)=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 253877Potassium BromideHCID 20827101{8-[4-(2,5-Dichloro-benzyloxy)-benzylsulfanyl]-chroman-5-yloxy}-acetic Acid Methyl Ester

Product 1

HCID 22280019{8-[4-(2,5-Dichloro-benzyloxy)-benzylsulfanyl]-chroman-5-yloxy}-acetic Acid

Procedure

The title compound was prepared in the manner analogous to Example 1 using 85A. mp 98-100° C.; IR (KBr) cm−1: 3038, 2854, 1729, 1508, 1240, 1124; 400 MHz 1H NMR (DMSO-d6): δ 12.95 (br(s), 1H), 7.57-7.62 (m, 1H), 7.39-7.53 (m, 2H); 7.12-7.20 (m, 2H), 6.84-6.96 (m, 3H), 6.26 (d, 1H, J=8.6 Hz), 5.05 (s, 2H), 4.58 (s, 2H), 4.09 (t, 2H, J=4.9 Hz), 3.92 (s, 2H), 2.55 (t, 2H, J=6.5 Hz), 1.83 (pentet, 2H); MS m/z 503 (M−1). Anal. Calc'd for C25H22Cl2O5S: C, 59.41; H, 4.39. found: C, 59.20; H, 4.20.

Sources & evidence

ORD record
ord-fe4fc6676cf741af8d8952fcbc718790
Source dataset
uspto-grants-2005_11
Patent number
US06964983B2

Reaction notes

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