2-Bromo-3'-chloroacetophenone → HCID 71536627, compound

HRID 1519272Notes

Reaction equation

HRID 1519272 reaction equation
C[O:2][C:3]([C:5]1[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N+:20]([O-:22])=[O:21])=[CH:7][CH:8]=[C:9]([C:11](=[S:13])[NH2:12])[CH:10]=1)=[O:4].[Cl:23][C:24]1[CH:25]=[C:26]([CH:31]=[CH:32][CH:33]=1)[C:27](=O)[CH2:28]Br>O>[Cl:23][C:24]1[CH:25]=[C:26]([C:27]2[N:12]=[C:11]([C:9]3[CH:10]=[C:5]([C:3]([OH:2])=[O:4])[C:6]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[N+:20]([O-:22])=[O:21])=[CH:7][CH:8]=3)[S:13][CH:28]=2)[CH:31]=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 387382-Bromo-3'-chloroacetophenoneHCID 866798322'-Nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester2×

Product 1

HCID 71536627HCID 71536627, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-[4-(3-Chloro-phenyl)-thiazol-2-yl]-2′-nitro-biphenyl-2-carboxylic acid (82 mg, 30%) was prepared from 2′-nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester (which may be prepared as described for Intermediate 4) and 3-chlorophenacyl bromide (available from Oakwood Products, Inc.) using the procedure described for the preparation of Example 18 except that the entire 4 mL of water was added at the beginning of the hydrolysis step rather than being added in two portions. 1H NMR (300 MHz, DMSO-d6) δ 13.12 (br s, 1H), 8.56 (d, J=1.7 Hz, 1H), 8.42 (s, 1H), 8.28 (dd, J=8.0, 1.9 Hz, 1H), 8.12-8.16 (m, 2H), 8.03-8.07 (m, 1H), 7.76-7.81 (m, 1H), 7.62-7.68 (m, 1H), 7.41-7.55 (m, 4H).

Workup

  1. additionwas added at the beginning of the hydrolysis step rather
  2. additionthan being added in two portions

Sources & evidence

ORD record
ord-bdc3da20370b46d8bb39c276da9cdc05
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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