Bromine → HCID 86755709, compound

HRID 1873162Notes

Reaction equation

HRID 1873162 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]([O:25][CH3:26])=[C:14]3[C:9]=2[CH:10]=[CH:11][CH:12]=[CH:13]3)[CH:5]=[C:4]([Br:27])[C:3]=1[OH:28].O[C@@H:30]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:31]([O:33][CH3:34])=[O:32].BrBr>>[Br:27][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]([O:25][CH3:26])=[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:28][C@H:30]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:31]([O:33][CH3:34])=[O:32]

Participants

4

Reactant 3

HCID 24408BromineHCID 5289077(S)-methyl 2-hydroxy-3-phenylpropanoateHCID 541257882,6-Dibromo-4-(6-methoxy-benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenol

Product 1

HCID 86755709HCID 86755709, compound

Procedure

Prepared from 2,6-dibromo-4-(6-methoxy-benzo[b]naphtho[2,3-d]thiophen-11-yl )-phenol (Example 63) and (S)-2-hydroxy-3-phenylpropionic acid, methyl ester (Example 96) according to the procedure of Example 107. White solid (0.608 g, 96%): NMR (THF-d8); δ8.29-8.26 (m, 1 H), 7.87 (d., J=8 Hz, 1 H), 7.72 - 7.68 (dd, 2 H, J=4, 2 Hz), 7.60 - 7.56 (m, 2 H), 7.48-7.37 (m, 4 H), 7.32 - 7.28 (m, 2 H), 7.25-7.23 (m, 2 H), 7.20 - 7.15 (m, 2 H), 6.85 - 6.82 (m, 1 H), 5.22(dd, 1 H, J=14, 2, Hz), 4.17 (s, 1 H), 3.71 (s, 1 H), 3.58(s, 6 H), ; MS (FAB+): [M+], 2 bromine isotope pattern, 674 (40%), 676 (66%), 678 (45%); Anal. Calc. for C33H24Br2O4S: C, 58.60, H, 3.58, N, 0.00. Found: C, 58.11, H, 3.53, N, 0.19.

Sources & evidence

ORD record
ord-93c0da1c9c27480b9dc4e410da5b6d43
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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