p-Bromoacetophenone → 1-[4-(4-fluorophenoxy)phenyl]ethanone

HRID 1576578Notes

Reaction equation

HRID 1576578 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Br[C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:18])[CH3:17])=[CH:12][CH:11]=1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:10]2[CH:15]=[CH:14][C:13]([C:16](=[O:18])[CH3:17])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 7466p-BromoacetophenoneHCID 97324-Fluorophenol

Product 1

HCID 27590561-[4-(4-fluorophenoxy)phenyl]ethanone

Procedure

The starting material was prepared as follows. An Ullmann reaction using p-fluorophenol and p-bromoacetophenone gave 4'-(4-fluorophenoxy)acetophenone, m.p. 65°-67°C. This was subjected to the Willgerodt reaction using morpholine and sulfur, followed by hydrolysis, to give crude 4-(4-fluorophenoxy)phenylacetic acid, which was esterified and gave ethyl 4-(4-fluorophenoxy)phenylacetate, b.p. 139°-142°C./0.3 mm. This ester was treated conventionally with diethyl carbonate and sodium ethoxide, and then with dimethyl sulfate, to yield the required ethyl 2-[4-(4-fluorophenoxy)phenyl]-2-methylmalonate, b.p. 174°-182°C./0.7 mm.

Workup

  1. customThe starting material was prepared
  2. customAn Ullmann reaction

Sources & evidence

ORD record
ord-b14ec83f7d95482e8f62862f30d7d4ed
Source dataset
uspto-grants-1976_09
Patent number
US03981905

Reaction notes

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