Benzene, 1-(chloromethyl)-2-fluoro- → HCID 178505635, compound

HRID 1678996Notes

Reaction equation

HRID 1678996 reaction equation
[OH:1][C@H:2]1[CH2:7][O:6][C@@H:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:4][CH2:3]1.[H-].[Na+].[Na].[F:17][C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH2:20]Cl>>[F:17][C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH2:20][O:1][C@H:2]1[CH2:3][O:4][C@@H:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:6][CH2:7]1

Participants

5

Reactant 4

HCID 9580Benzene, 1-(chloromethyl)-2-fluoro-HCID 24758Sodium hydrideHCID 5360545SodiumHCID 178521647HCID 178521647, compound

Product 1

HCID 178505635HCID 178505635, compound

Procedure

Using the method of Example 8, cis-5-hydroxy-2-phenyl-1,3-dioxane (8.4 g, 0.047 mole) was reacted with sodium hydride (2.0 g of 61%, 0.047 mole). The reactant sodium salt was reacted with 2-fluorobenzyl chloride (7.2 g, 0.05 mole) to give, after recrystallization from benzene-ligroin, 2.8 g of white solid, m.p. 65°-67° C, and on further recrystallization, a solid, m.p. 70°-71° C. Analysis by VPC indicated the product to be 90% cis-5-(2-fluorobenzyloxy)-2-phenyl-1,3-dioxane.

Workup

  1. customto give
  2. customafter recrystallization from benzene-ligroin, 2.8 g of white solid, m.p. 65°-67° C
  3. customon further recrystallization

Sources & evidence

ORD record
ord-6e22976348514930b5b30508e42d842c
Source dataset
uspto-grants-1978_03
Patent number
US04077982

Reaction notes

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