Bromine → HCID 18687879, compound

HRID 1873177Notes

Reaction equation

HRID 1873177 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]([I:25])=[C:14]3[C:9]=2[CH:10]=[CH:11][CH:12]=[CH:13]3)[CH:5]=[C:4]([Br:26])[C:3]=1[OH:27].O[C@@H:29]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:30]([O:32]C)=[O:31].BrBr>C(Cl)(Cl)Cl>[Br:26][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]([I:25])=[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:27][CH:29]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:30]([OH:32])=[O:31]

Participants

5

Reactant 3

HCID 24408BromineHCID 5289077(S)-methyl 2-hydroxy-3-phenylpropanoateHCID 15481273HCID 15481273, compound

Product 1

HCID 18687879HCID 18687879, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Prepared from of 2,6-dibromo-4-(6-iodo-benzo[b]naphtho[2,3-d]thiophen-11 -yl)-phenol (Example 59) and (S)-2-hydroxy-3-phenylpropionic acid, methyl ester (Example 96). White solid: [a]25/D=+31.791° (9.940 mg/mL CHCl3); NMR (CDCl3); δ8.23 (ddd, J=8, 1, 1 Hz), 7.81 (ddd, J=8, 1, 1 Hz, 1 H), 7.64 (ddd, J=8,7, 1 Hz, 1 H), 7.58 (dd, J=9, 2Hz, 2 H), 7.52-7.39 (m, 7 H), 7.37-7.28 (m, 2 H), 6.68 (ddd, J=8,1, 1 Hz, 1 H), 5.48 (t, J=7 Hz, 1 H, -CH), 3.5 (d, J=7 Hz, 2 H); MS (+FAB): [M+], 2 bromine isotope pattern, 756 (65%), 758 (100%), 760 (90%); Anal. calc. for C31H19Br2IO3S: C, 49.10, H, 2.53, N, 0.00. Found: C, 50.75, H, 3.00, N, 0.09.

Sources & evidence

ORD record
ord-55b91746a0eb46d08f02fb0c80a1fce0
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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