Bromine → HCID 53968183, compound

HRID 1873172Notes

Reaction equation

HRID 1873172 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]2[C:17]3[C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[S:20][C:16]=3[C:15]([S:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[C:14]3[C:9]=2[CH:10]=[CH:11][CH:12]=[CH:13]3)[CH:5]=[C:4]([Br:32])[C:3]=1[OH:33].O[C@@H:35]([CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:36]([O:38]C)=[O:37].BrBr>>[Br:32][C:4]1[CH:5]=[C:6]([C:8]2[C:17]3[C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[S:20][C:16]=3[C:15]([S:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[C:14]3[C:9]=2[CH:10]=[CH:11][CH:12]=[CH:13]3)[CH:7]=[C:2]([Br:1])[C:3]=1[O:33][C@H:35]([CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:36]([OH:38])=[O:37]

Participants

4

Reactant 3

HCID 24408BromineHCID 5289077(S)-methyl 2-hydroxy-3-phenylpropanoateHCID 18687830HCID 18687830, compound

Product 1

HCID 53968183HCID 53968183, compound

Procedure

Prepared from of 2,6-dibromo-4-(6-phenylsulfanyl-benzo[b]naphtho[2,3-d ]thiophen-11-yl)-phenol (Example 64) and (S)-2-hydroxy-3-phenylpropionic acid, methyl ester (Example 96). White solid: NMR (DMSO-d6); δ8.50 (d, J=8 Hz, 1 H), 7.98 (d, J=8 Hz, 1 H), 7.83 (d, J=2 Hz, 1 H), 7.81 (d, J=2 Hz, 1 H),7.71 (ddd, J=6, 5, 2 Hz, 2 H), 7.58 (m, 2 H), 7.47 (ddd, J=8, 8, 1 Hz, 1 H), 7.42 (d, J=8 Hz, 2 H), 7.34 (t, J=7 Hz, 2 H), 7.29-7.20 (m, 4 H), 7.17-7.08 (m, 3 H), 6.67 (d, J=8 Hz, 1 H), 5.35 (t, J=7 Hz, 1 H, CH), 3.41 (d, J=7 Hz, 2 H); MS (+FAB): [M+], 2 bromine isotope pattern, 738 (35%), 740 (90%) 742 (60%); Anal. Calc. for C37H24Br203S2: C, 60.01, H, 3.27, N, 0.00. Found: C, 58.57, H, 3.04, N, 0.22.

Sources & evidence

ORD record
ord-d4454774e6e24daa99178aa63e823e96
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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