(3-Bromophenyl)acetic acid → Methyl 2-(3-bromophenyl)acetate

HRID 218228Notes

Reaction equation

HRID 218228 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.Cl.[CH3:13]N(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.CO>[CH3:13][O:10][C:9](=[O:11])[CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1

Participants

5

Reactant 2

HCID 74653(3-Bromophenyl)acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 11746402Methyl 2-(3-bromophenyl)acetate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-bromophenylacetic acid (2.0 g, 9.3 mmol) and 4-dimethylamino pyridine (1.1 g, 9.3 mmol) in methanol (20 mL) was treated with N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDAC) (2.1 g, 11 mmol). Reaction stirred for 16 hours at room temperature. The reaction mixture was concentrated under reduced pressure. The residue was taken up in ethyl acetate and washed with water, saturated sodium bicarbonate, 1N phosphoric acid, and brine before drying over Na2SO4, filtering, and concentrating under reduced pressure to provide the title compound.

Workup

  1. customReaction
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. washwashed with water, saturated sodium bicarbonate, 1N phosphoric acid, and brine
  4. dry with materialbefore drying over Na2SO4
  5. filtrationfiltering
  6. concentrationconcentrating under reduced pressure

Sources & evidence

ORD record
ord-8b58122e3aa142f682c9f941729e1a92
Source dataset
uspto-grants-2012_06
Patent number
US08198331B2

Reaction notes

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