Bromine → HCID 9896243, compound

HRID 1873176Notes

Reaction equation

HRID 1873176 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].[C:28]([O:33]C)(=[O:32])[C@H:29]([CH3:31])O.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][C@H:29]([CH3:31])[C:28]([OH:33])=[O:32]

Participants

5

Reactant 3

HCID 24408BromineHCID 94386methyl (S)-lactateHCID 15481273HCID 15481273, compound

Product 1

HCID 9896243HCID 9896243, 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 commercially available (S)-lactic acid, methyl ester. White solid: mp 129-196° C. dec; Opt. rot. [a]25/D=+4.312° (8.812 mg/mL, CHCl3); NMR (DMSO-d6); δ13.12 (broad s, 1 H), 8.12 (d, J=8, 1 Hz, 1 H), 8.06 (d, J =7 Hz, 1 H), 7.82 (q, J=Hz, 2 H), 7.75 (ddd, J=8,7, 1 Hz, 1 H), 7.62-7.49 (m, 3 H), 7.27 (ddd, J=8, 7, 1 Hz, 1 H), 6.61 (d, J=8 Hz, 1 H), 5.12 (q, J=7 Hz, 1 H), 1.63 (d, J =7 Hz, 3 H); MS (+FAB): [M+], 2 bromine isotope pattern, 680 (45%), 682 (100%), 684 (60%); Anal. Calc. for C25H15Br2IO3S: C, 44.02, H, 2.22, N, 0.00; Found: C, 44.66, H, 2.54, N, 0.21.

Sources & evidence

ORD record
ord-323ec3ea8bce46788f8058c162912dba
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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