Dichloromethane → HCID 21217011, compound

HRID 1586527Notes

Reaction equation

HRID 1586527 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6](CO)=[C:5]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[C:4]=1[C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1.S(Cl)([Cl:27])=O.[CH2:29]([Cl:31])Cl>N1C=CC=CC=1>[Cl:27][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:29][Cl:31])=[C:5]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[C:4]=1[C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 21217012HCID 21217012, compound

Product 1

HCID 21217011HCID 21217011, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 1049PyridineCatalyst

Procedure

A 250 mL 3 neck round-bottom flask equipped with a condenser was flushed with nitrogen and then loaded with 1,4-bis(hydroxymethyl)-2,3-di-(4-fluorophenyl)-benzene (2.70 g, 8.28 mmol), thionyl chloride (2.20 g, 18.5 mmol), methylene chloride (90 mL) and 3 drops of pyridine. The solution was then refluxed overnight and then cooled to room temperature. Methylene chloride was removed by rotary evaporation and then methanol was added to precipitate out the white product (0.77 g, 26% yield).

Workup

  1. customwas flushed with nitrogen
  2. temperatureThe solution was then refluxed overnight
  3. customMethylene chloride was removed by rotary evaporation
  4. additionmethanol was added

Sources & evidence

ORD record
ord-b879e2b1a2914e1683e1c26eb73386aa
Source dataset
uspto-grants-1999_08
Patent number
US05945502

Reaction notes

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