Ethyl bromoacetate → Ethyl 2-(4-((3r,5r,7r)-adamantan-1-yl)phenoxy)acetate

Reaction equation

Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:8]12([C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2>>[CH2:6]([O:5][C:3](=[O:4])[CH2:2][O:24][C:21]1[CH:20]=[CH:19][C:18]([C:8]23[CH2:9][CH:10]4[CH2:16][CH:14]([CH2:13][CH:12]([CH2:11]4)[CH2:17]2)[CH2:15]3)=[CH:23][CH:22]=1)[CH3:7]

Participants

Reactant 2

HCID 7748Ethyl bromoacetate

HCID 2699334-(1-Adamantyl)phenol

Product 1

HCID 3108472Ethyl 2-(4-((3r,5r,7r)-adamantan-1-yl)phenoxy)acetate

Procedure

Analogously to the method described in Example 16, the use of ethyl bromoacetate and p-(1-adamantyl)-phenol as starting materials gives 4-(1-adamantyl)-phenoxyacetic acid ethyl ester of melting point 89°-90° C (flakes; from etherpentane).

Sources & evidence

ORD record: ord-5c8edeac720c48ae8dc4ae7d1cbdaed6
Source dataset: uspto-grants-1977_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04035413

Reaction notes

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