Water → HCID 19013818, compound

HRID 1728508Notes

Reaction equation

HRID 1728508 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([CH:24](Br)[CH:25](Br)[CH3:26])=[C:20]([F:29])[C:19]=3[F:30])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].O>COC(C)(C)C>[CH2:1]([C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([C:24]#[C:25][CH3:26])=[C:20]([F:29])[C:19]=3[F:30])=[CH:14][CH:13]=2)=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 962WaterHCID 19013808HCID 19013808, compound

Product 1

HCID 19013818HCID 19013818, compoundYield 67.9%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

2.5 g of potassium tert.butylate are added to a solution of 4.3 g of crude 1-[4-(4-pentylphenyl)-phenyl]-2,3-difluoro-4-(1,2-dibromopropyl)-benzene in 200 ml of tert.butyl methyl ether and the reaction mixture is heated at reflux temperature for 4.5 hours. Thereafter, it is cooled, treated with 50 ml of water and partitioned between water and diethyl ether. The combined organic phases are dried over anhydrous magnesium sulphate, the solvent is evaporated and the residue is chroma-tograped on silica gel with 5% ethyl acetate in petroleum ether. Filtration over Alox (CAMAG, neutral, activity grade 1) and fractional crystallization from ethyl acetate gives 2.04 g of 1-[4-(4-pentylphenyl)-phenyl]-2,3-difluoro-4-(1-propynyl)-benzene, m.p. (C-SB) 135.7° C.; SB -N 173° C.; cl.p. (N-I) about 210° C.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureat reflux temperature for 4.5 hours
  3. temperatureThereafter, it is cooled
  4. custompartitioned between water and diethyl ether
  5. dry with materialThe combined organic phases are dried over anhydrous magnesium sulphate
  6. customthe solvent is evaporated
  7. filtrationFiltration
  8. customover Alox (CAMAG, neutral, activity grade 1) and fractional crystallization from ethyl acetate

Sources & evidence

ORD record
ord-265ba2b1583745569bcf587c16f8ba70
Source dataset
uspto-grants-1994_07
Patent number
US05328637

Reaction notes

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