Bromine → HCID 9874542, compound

HRID 1873171Notes

Reaction equation

HRID 1873171 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]([Cl: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.ClCl>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]([Cl: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]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:30]([OH:32])=[O:31]

Participants

6

Reactant 4

HCID 24408BromineHCID 24526ChlorineHCID 5289077(S)-methyl 2-hydroxy-3-phenylpropanoateHCID 15481274HCID 15481274, compound

Product 1

HCID 9874542HCID 9874542, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Prepared from of 2,6-dibromo-4-(6-chloro-benzo[b]naphtho[2,3-d]thiophen-11 -yl)-phenol (Example 60) and (S)-2-hydroxy-3-phenylpropionic acid, methyl ester (Example 96). White solid: [a]25/D=+19.63° (8.805 mg/mL, CHCl3); NMR (DMSO-d 6); δ13.25-13.22 (broad singlet, 1 H), 8.32 (d, J=8 Hz, 1 H,), 8.70 (d, J=8 Hz, 1 H), 7.81-7.79 (ddd, J=8,7, 1 Hz, 1 H), 7.79 (dd, J 10, 2 Hz, 2 H), 7.64 (ddd, J=8,7, 1 Hz, 1 H), 7.58-7.49 (m, 2 H), 7.42-7.32 (m, 4 H, ), 7.29-7.24 (m, 2 H), 6.66 (d, J=8 Hz, 1 H), 5.32 (t, J=6 Hz, 1 H,), 3.41 (d, J=7 Hz, 2 H); MS (-ESI): [(M-H)+], 2 bromine, 1 chlorine isotope pattern, 663 (40%),665 (100%), 667 (60%), 669 (17%); Anal Calc. for C31H19Br2ClO3S: C, 55.84, H, 2.87, N, 0.00. Found: C, 56.95; H, 3.00, N, 0.24.

Sources & evidence

ORD record
ord-030e4f29f3bc4f5484f8d885d51359b3
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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