Bromine → 1-(4-Bromophenyl)cyclopropane-1-carboxylic acid

HRID 1365596Notes

Reaction equation

HRID 1365596 reaction equation
[Br:1]Br.[C:3]1([C:9]2([C:12]([OH:14])=[O:13])[CH2:11][CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([O-])(=O)C.[Na+]>C(O)(=O)C.O>[Br:1][C:6]1[CH:7]=[CH:8][C:3]([C:9]2([C:12]([OH:14])=[O:13])[CH2:11][CH2:10]2)=[CH:4][CH:5]=1

Participants

6

Reactant 3

HCID 24408BromineHCID 802061-Phenylcyclopropanecarboxylic acidHCID 517045Sodium Acetate

Product 1

HCID 162279661-(4-Bromophenyl)cyclopropane-1-carboxylic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

At 5° C. bromine (1.5 mL, 30 mmol) is added dropwise to a solution of 1-phenyl-1-cyclopropylcarboxylic acid (5 g, 30 mmol) and sodiumacetate (2.7 g, 33 mmol) in 30 mL glacial acetic acid. Then the mixture is heated to 50° C. and stirred for 2 days. The reaction mixture is diluted with 100 mL water, and the precipitate formed is filtered off and washed with 50% acetic acid. Yield: 5.7 g.

Workup

  1. customthe precipitate formed
  2. filtrationis filtered off
  3. washwashed with 50% acetic acid

Sources & evidence

ORD record
ord-db5340697437400a9021f901e0e37d97
Source dataset
uspto-grants-2011_02
Patent number
US07893049B2

Reaction notes

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