2-Bromo-2'-fluoroacetophenone → HCID 71536629, compound

HRID 1519277Notes

Reaction equation

HRID 1519277 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].[F:23][C:24]1[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=1[C:26](=O)[CH2:27]Br>O>[F:23][C:24]1[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=1[C:26]1[N:12]=[C:11]([C:9]2[CH:10]=[C:5]([C:3]([OH:2])=[O:4])[C:6]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N+:20]([O-:22])=[O:21])=[CH:7][CH:8]=2)[S:13][CH:27]=1

Participants

4

Reactant 2

HCID 27374492-Bromo-2'-fluoroacetophenoneHCID 866798322'-Nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester2×

Product 1

HCID 71536629HCID 71536629, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-[4-(2-Fluoro-phenyl)-thiazol-2-yl]-2′-nitro-biphenyl-2-carboxylic acid (46 mg, 18%) was prepared from 2′-nitro-4-thiocarbamoyl-biphenyl-2-carboxylic acid methyl ester (which may be prepared as described for Intermediate 4) and 2-fluorophenacyl bromide (available from Matrix Scientific) 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 8.57 (d, J=1.8 Hz, 1H), 8.12-8.30 (m, 4H), 7.61-7.80 (m, 2H), 7.34-7.50 (m, 5H).

Workup

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

Sources & evidence

ORD record
ord-2cf5682403a641e399d8cb0ea34fe8fc
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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