2-Bromo-1-(2,4-dichlorophenyl)ethanol → HCID 54124894, compound

HRID 905074Notes

Reaction equation

HRID 905074 reaction equation
[Br:1][CH2:2][CH:3]([OH:12])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[Cl:11].[Cl:13][C:14]1[CH:28]=[CH:27][C:17]([CH2:18][O:19][CH2:20][CH:21]2[CH2:26][CH2:25][CH:24]=[CH:23][O:22]2)=[CH:16][CH:15]=1>C(OCC)C.O=P(Cl)(Cl)Cl>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:18][O:19][CH2:20][C@@H:21]2[O:22][C@@H:23]([O:12][CH:3]([C:4]3[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=3[Cl:11])[CH2:2][Br:1])[CH2:24][CH2:25][CH2:26]2)=[CH:27][CH:28]=1

Participants

5

Reactant 2

HCID 133860712-Bromo-1-(2,4-dichlorophenyl)ethanolHCID 204769372-(4-chlorobenzyloxymethyl)-3,4-dihydro-2H-pyran

Product 1

HCID 54124894HCID 54124894, compoundYield 69.2%

Reagents, catalysts & solvents 2

HCID 24813Phosphorus oxychlorideCatalystHCID 3283Diethyl EtherSolvent

Procedure

102 mg of α-bromomethyl-2,4-dichlorobenzyl alcohol and the 82 mg of 2-(4-chlorobenzyloxymethyl)-3,4-dihydro-2H-pyran prepared above were then dissolved in 2 ml of diethyl ether, and one drop of phosphorus oxytrichloride was then added. The mixture was then allowed to react at room temperature for 4 days, after which it was treated and the product purified essentially as described in Example 34(a), to give 121 mg of trans-6-(4-chlorobenzyloxymethyl)-2-[2-bromo-1-(2,4-dichlorophenyl)ethoxy]tetrahydropyran.

Workup

  1. customto react at room temperature for 4 days
  2. additionafter which it was treated
  3. customthe product purified essentially

Sources & evidence

ORD record
ord-5404afa93e2540fd86b2d35fa5326034
Source dataset
uspto-grants-1983_12
Patent number
US04421758

Reaction notes

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