2-Bromo-1-(4-fluorophenyl)ethan-1-one → HCID 13732571, compound

HRID 1731546Notes

Reaction equation

HRID 1731546 reaction equation
C[O-].[Na+].C([S:7][CH2:8][CH2:9][N:10]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=[O:20])(=O)C.[CH:21]1[C:26]([C:27]([CH2:29]Br)=[O:28])=[CH:25][CH:24]=[C:23]([F:31])[CH:22]=1>C(O)C>[F:31][C:23]1[CH:24]=[CH:25][C:26]([C:27]([CH2:29][S:7][CH2:8][CH2:9][N:10]2[C:11](=[O:20])[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:18]2=[O:19])=[O:28])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-oneHCID 120998S-[2-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl] ethanethioateHCID 10942334Sodium Methoxide

Product 1

HCID 13732571HCID 13732571, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

0.803 kg (14.8M) sodium methoxide in 16 1 of ethanol is added to a stirred solution of 3.7 kg (14.8M) 2-(acetylthioethyl)-1,3-isoindoledione in 29.2 1 ethanol at 0° . The temperature is maintained between 0°-5° and the reaction mixture is stirred for one hour. 3.23 kg (14.8M) a-bromo-4-fluoroacetophenone in 14.6 1 of ethanol is added at such a rate to maintain the temperature between 0° and 10° . The reaction mixture is stirred overnight at room temperature. The product is collected by filtration, washed with ethanol and ether and dried. M.P. 123.5°-125.5°.

Workup

  1. temperatureThe temperature is maintained between 0°-5°
  2. temperatureto maintain the temperature between 0° and 10°
  3. stirringThe reaction mixture is stirred overnight at room temperature
  4. filtrationThe product is collected by filtration
  5. washwashed with ethanol and ether
  6. customdried

Sources & evidence

ORD record
ord-1cddbca8d3f844148404aae0436de7f7
Source dataset
uspto-grants-1986_11
Patent number
US04622322

Reaction notes

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