2-Bromomethylnaphthalene → HCID 19761518, compound

HRID 654556Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([OH:15])[CH:5]=[C:6]([C:8]([O:13][CH3:14])([CH:10]([OH:12])[CH3:11])[CH3:9])[CH:7]=1.Br[CH2:17][C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=1>>[F:1][C:2]1[CH:3]=[C:4]([O:15][CH2:17][C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=2)[CH:5]=[C:6]([C:8]([O:13][CH3:14])([CH:10]([OH:12])[CH3:11])[CH3:9])[CH:7]=1

Participants

Reactant 2

HCID 703202-Bromomethylnaphthalene

HCID 19761553HCID 19761553, compound

Product 1

HCID 19761518HCID 19761518, compoundYield 94%

Procedure

Using the procedure described in Example 12, (2RS,3SR)-2-(5-fluoro-3-hydroxyphenyl)-2-methoxybutan-3-ol was reacted with 2-bromomethylnaphthalene to give (2RS,3SR)-2-[5-fluoro-3-(naphth-2-ylmethoxy)phenyl]-2-methoxybutan-3-ol in 94% yield, m.p. 62°-63° C.

Sources & evidence

ORD record: ord-7b50ea3a5a7f4fa4a4201b32d9b0011c
Source dataset: uspto-grants-1992_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05132328

Reaction notes

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