Dichloromethane → HCID 21217015, compound

HRID 1586530Notes

Reaction equation

HRID 1586530 reaction equation
[CH2:1]([C:7]1[C:8](CO)=[C:9]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[C:10]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[C:11]([CH2:13]O)[CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].S(Cl)([Cl:33])=O.[CH2:35]([Cl:37])Cl>>[CH2:1]([C:7]1[C:8]([CH2:35][Cl:37])=[C:9]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[C:10]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[C:11]([CH2:13][Cl:33])[CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 21217003HCID 21217003, compound

Product 1

HCID 21217015HCID 21217015, compoundYield 74.7%

Procedure

A 250 mL 3 neck round-bottom flask equipped with a condenser was flushed with nitrogen and then loaded with 5-hexyl-1,4-bis(hydroxymethyl)-2,3-di(4-fluorophenyl)-benzene (1.35 g, 3.3 mmol), thionyl chloride (7 g, 58.8 mmol) and methylene chloride (10 mL) was stirred at room temperature for 1 hour, and then refluxed for an additional 2 hour, and finally stirred at room temperature overnight. The solvent was then removed by rotary evaporation to give a pale yellow oil (1.1 g, 74.7% yield).

Workup

  1. customwas flushed with nitrogen
  2. temperaturerefluxed for an additional 2 hour
  3. stirringfinally stirred at room temperature overnight
  4. customThe solvent was then removed by rotary evaporation

Sources & evidence

ORD record
ord-43ea999a068645338ea0e1593d55eafd
Source dataset
uspto-grants-1999_08
Patent number
US05945502

Reaction notes

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