2-Bromo-1-(2,4-dichlorophenyl)ethanol → trans-6-(4-Fluorophenoxymethyl)-2-[2-bromo-1-(2,4-dichlorophenyl)ethoxy]tetrahydropyran

HRID 905072Notes

Reaction equation

HRID 905072 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].[F:13][C:14]1[CH:27]=[CH:26][C:17]([O:18][CH2:19][CH:20]2[CH2:25][CH2:24][CH:23]=[CH:22][O:21]2)=[CH:16][CH:15]=1>C(OCC)C.O=P(Cl)(Cl)Cl>[F:13][C:14]1[CH:15]=[CH:16][C:17]([O:18][CH2:19][C@@H:20]2[O:21][C@@H:22]([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])[CH2:23][CH2:24][CH2:25]2)=[CH:26][CH:27]=1

Participants

5

Reactant 2

HCID 133860712-Bromo-1-(2,4-dichlorophenyl)ethanolHCID 204769402-(4-fluorophenoxymethyl)-3,4-dihydro-2H-pyran

Product 1

HCID 53973166trans-6-(4-Fluorophenoxymethyl)-2-[2-bromo-1-(2,4-dichlorophenyl)ethoxy]tetrahydropyran

Reagents, catalysts & solvents 2

HCID 24813Phosphorus oxychlorideCatalystHCID 3283Diethyl EtherSolvent

Procedure

389 mg of α-bromomethyl-2,4-dichlorobenzyl alcohol and 300 mg of 2-(4-fluorophenoxymethyl)-3,4-dihydro-2H-pyran, prepared as described above, were dissolved in 10 ml of diethyl ether. A catalytic amount (2 drops) of phosphorus oxytrichloride was added to the resulting solution and the mixture 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 214 mg of the isomer of lesser polarity of trans-6-(4-fluorophenoxymethyl)-2-[2-bromo-1-(2,4-dichlorophenyl)ethoxy]tetrahydropyran, 211 mg of the isomer of greater polarity and 143 mg of a mixture of these isomers.

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-19e8598fbe644e7d8d93f71e65834ade
Source dataset
uspto-grants-1983_12
Patent number
US04421758

Reaction notes

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