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

HRID 643962Notes

Reaction equation

HRID 643962 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-98d735d0b58841678711e36b538cbf5a
Source dataset
uspto-grants-2010_04
Patent number
US07700635B2

Reaction notes

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