Benzyl Bromide → 6-{2-[2,4-Dichloro-6-(4-trifluoromethylphenylmethoxy)phenyl]ethyl}-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-one

HRID 354577Notes

Reaction equation

HRID 354577 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([OH:9])[C:3]=1[CH2:10][CH2:11][CH:12]1[O:17][C:16](=[O:18])[CH2:15][CH:14]([OH:19])[CH2:13]1.[F:20][C:21]([F:31])([F:30])[C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Br)=[CH:24][CH:23]=1.ClC1C=C(O)C(=C(Cl)C=1)C=O.C(Br)C1C=CC=CC=1>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([O:9][CH2:26][C:25]2[CH:24]=[CH:23][C:22]([C:21]([F:20])([F:30])[F:31])=[CH:29][CH:28]=2)[C:3]=1[CH2:10][CH2:11][CH:12]1[O:17][C:16](=[O:18])[CH2:15][CH:14]([OH:19])[CH2:13]1

Participants

5

Reactant 4

HCID 7498Benzyl BromideHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 5283902,4-Dichloro-6-hydroxybenzaldehydeHCID 135531966-{2-(2,4-Dichloro-6-hydroxyphenyl)-ethyl}-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-one

Product 1

HCID 131860456-{2-[2,4-Dichloro-6-(4-trifluoromethylphenylmethoxy)phenyl]ethyl}-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-one

Procedure

By following the procedure of Example 1, step A, but substituting equimolar amounts of 6-{2-(2,4-dichloro-6-hydroxyphenyl)ethyl}-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-one and 4-trifluoromethylbenzyl bromide for the 4,6-dichlorosalicylaldehyde and benzyl bromide used therein, the title compound is obtained, m.p. 104°-105° C.

Sources & evidence

ORD record
ord-5e1be130cf9d4f8db5a5786fe1ce6da7
Source dataset
uspto-grants-1983_03
Patent number
US04375475

Reaction notes

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