Bromine → HCID 9939918, compound

HRID 1873170Notes

Reaction equation

HRID 1873170 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]([C:25]([F:28])([F:27])[F:26])=[C:14]3[C:9]=2[CH:10]=[CH:11][CH:12]=[CH:13]3)[CH:5]=[C:4]([Br:29])[C:3]=1[OH:30].O[C@@H:32]([CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:33]([O:35]C)=[O:34].BrBr>CO>[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]([C:25]([F:27])([F:28])[F:26])=[C:14]3[C:9]=2[CH:10]=[CH:11][CH:12]=[CH:13]3)[CH:5]=[C:4]([Br:29])[C:3]=1[O:30][C@H:32]([CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:33]([OH:35])=[O:34]

Participants

5

Reactant 3

HCID 24408BromineHCID 5289077(S)-methyl 2-hydroxy-3-phenylpropanoateHCID 18687799HCID 18687799, compound

Product 1

HCID 9939918HCID 9939918, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepared from of 2,6-dibromo-4-(6-trifluoromethyl-benzo[b]naphtho[2,3-d ]thiophen-11-yl)-phenol (Example 61) and (S)-2-hydroxy-3-phenylpropionic acid, methyl ester (Example 96). White solid: mp 109-143° C.; [a]D25=+47.99° (10.002 mg/mL CH3OH); NMR (DMSO-d6); δ13.26 (s, 1 H), 8.30 - 8.27 (m, 1 H), 8.06 (d, J =7 Hz, 1 H), 7.87 - 7.81 (m, 3 H), 7.71 - 7.60 (m, 2 H), 7.52 (dd, J=8, 1 Hz, 1 H), 7.43 -7.24 (m, 6 H), 6.60 (d, J=8 Hz, 1 H), 5.33 (t, J=7 Hz, 1 H), 3.41 (d, J=7 Hz, 2 H); MS (EI): [M+], 2 bromine isotope pattern, 698 (8%), 700 (20%) 702 (15%); Anal. Calc. for C32H19Br2F3O3S: C, 54.88, H, 2.74, N, 0.00. Found: C, 55.29, H, 3.11, N, 0.10.

Sources & evidence

ORD record
ord-ce81ad7694954468aaeaff81c76d2df2
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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