Bromine → HCID 10146115, compound

HRID 1278810Notes

Reaction equation

HRID 1278810 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]2[C:20]3[C:19]([CH3:21])=[C:18]([CH3:22])[S:17][C:16]=3[C:15]([S:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[C:14]3[C:9]=2[CH:10]=[CH:11][CH:12]=[CH:13]3)[CH:5]=[C:4]([Br:30])[C:3]=1[OH:31].[C:32]([O:37]C)(=[O:36])[C@H:33]([CH3:35])O.BrBr>C(Cl)(Cl)Cl>[Br:30][C:4]1[CH:5]=[C:6]([C:8]2[C:20]3[C:19]([CH3:21])=[C:18]([CH3:22])[S:17][C:16]=3[C:15]([S:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=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:31][C@H:33]([CH3:35])[C:32]([OH:37])=[O:36]

Participants

5

Reactant 3

HCID 24408BromineHCID 94386methyl (S)-lactateHCID 9808129HCID 9808129, compound

Product 1

HCID 10146115HCID 10146115, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Prepared from 2,6-dibromo-4-(2,3-dimethyl-9-phenylsulfanyl-naphtho[2,3-b]thiophen-4-yl)-phenol (Example 13) and and commercially available methyl (S)-(−)-lactate according to the procedure of Example 30. White solid: mp 237-239° C.; [a]25/D=−1.99° (10.051 mg 1 mL, CHCl3); NMR (DMSO-d6); δ 13.2 (broad s, 1H, COOH), 8.43 (d, J=8 Hz, 1H), 7.80 (s, 2H), 7.62-7.58 (m, 1H), 7.56-7.50 (m, 2H), 7.23-7.13 (m, 3H), 7.04-7.01 (m, 2H), 5.03 (quartet, J=7 Hz, 1H), 2.40 (s, 3H), 1.63 (s, 3H), 1.57 (d, J=8 Hz, 3H); MS (EI): [M+], 2 bromine isotope pattern, 640 (47%), 642 (100%), 644 (56%); Anal. calc. for C29H22Br2O3S2: C, 54.22, H, 3.45, N, 0.00. Found: C, 53.64, H, 3.33, N, 0.05.

Sources & evidence

ORD record
ord-1e80151a3a954609a7538cb681a8b9a2
Source dataset
uspto-grants-2002_09
Patent number
US06444670B2

Reaction notes

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