Bromine → (R)-2-[2,6-Dibromo-4-(6-bromo-benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenoxy]-propionic acid

HRID 1873168Notes

Reaction equation

HRID 1873168 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]([Br: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>>[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]([Br: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

4

Reactant 3

HCID 24408BromineHCID 94386methyl (S)-lactateHCID 108406542,6-Dibromo-4-(6-bromo-benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenol

Product 1

HCID 9809490(R)-2-[2,6-Dibromo-4-(6-bromo-benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenoxy]-propionic acid

Procedure

Prepared from of 2,6-dibromo-4-(6-bromo-benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenol (Example 21) and commercially available (S)-lactic acid, methyl ester. White solid: mp 131-133 ° C.: NMR (CDCl3);δ8.37 (d, J=9 Hz, 1 H), 7.84 (d, J=8 Hz, 1 H), 7.71-7.65 (m, 3 H), 7.57-7.50(m, 2 H), 7.45 (ddd, J=8, 7, 1 Hz, 1 H), 7.18 (ddd, J=8,7, 1 Hz, 1 H), 6.73 (d, J=8 Hz, 1 H), 5.36 (q, J=7 Hz, 1 H), 1.82 (d, J=7 Hz, 3 H); MS (EI): [M-H]+, 3 bromine isotope pattern, 631 (14%), 633 (44 %), 635 (42%), 637 (16%); Anal. Calc. for C25H15Br3O3S: C, 47.27, H, 2.38, N, 0.00. Found: C, 47.57, H, 2.33, N, 0.03.

Sources & evidence

ORD record
ord-a1a8cd6a36ee4797b0214ca1c11e53cc
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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