Diethyl Ether → 2-[4-(2-bromoacetyl)phenoxy]acetic Acid

HRID 1766211Notes

Reaction equation

HRID 1766211 reaction equation
[C:1]([C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[Br:15]Br.C(OCC)C>C(O)(=O)C>[Br:15][CH2:2][C:1]([C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:6][CH:5]=1)=[O:3]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24408Bromine2×HCID 74655(p-Acetylphenoxy)acetic acid

Product 1

HCID 49662-[4-(2-bromoacetyl)phenoxy]acetic AcidYield 46%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-(4-acetylphenoxy)acetic acid (2.81 g, 14.5 mmol) was dissolved in acetic acid (100 mL) and treated with bromine (740 μL, 14.5 mmol) and stirred 48 hours. Bromine (370 mL, 7.25 mmol) was added and solution was stirred for an additional 16 hours. Volatiles were removed under reduced pressure to provide a brown solid which was titurated with diethyl ether to provide 2-(4-(2-bromoacetyl)phenoxy)acetic acid (1.82 g) as a light brown solid.

Workup

  1. stirringsolution was stirred for an additional 16 hours
  2. customVolatiles were removed under reduced pressure
  3. customto provide a brown solid which

Sources & evidence

ORD record
ord-7be3992e08f04d2f822cdbd3dc599e5c
Source dataset
uspto-grants-2007_06
Patent number
US07230019B2

Reaction notes

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