Ethyl bromoacetate → HCID 45097190, compound

HRID 1393071Notes

Reaction equation

HRID 1393071 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH2:8][C:9]1[CH:10]=[C:11]([CH3:16])[C:12]([OH:15])=[CH:13][CH:14]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C.BrCC(OCC)=O>[CH2:6]([O:5][C:3](=[O:4])[CH2:2][O:15][C:12]1[CH:13]=[CH:14][C:9]([NH2:8])=[CH:10][C:11]=1[CH3:16])[CH3:7]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 760815-Amino-2-hydroxytoluene

Product 1

HCID 45097190HCID 45097190, compoundYield 106.3%

Reagents, catalysts & solvents 2

HCID 7748Ethyl bromoacetateCatalystHCID 6342AcetonitrileSolvent

Procedure

A solution of ethyl bromoacetate (7.19 ml, 63 mmol) and 4-amino-o-cresol (7.39 g, 60 mmol) in dry acetonitrile (420 ml) was treated at 15° C. with Cs2CO3 (42.03 g, 129 mmol) and stirred at RT for 2 h. Additional ethyl bromoacetate (0.33 ml, 3 mmol) was added and after 4 h, the mixture was filtered, washed with acetonitrile and evaporated. The residue was suspended in CH2Cl2, filtered and evaporated to give 13.34 g (quantitative) of (4-amino-2-methyl-phenoxy)-acetic acid ethyl ester as a green oil, MS: 210 (MH+).

Workup

  1. filtrationthe mixture was filtered
  2. washwashed with acetonitrile
  3. customevaporated
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-90070c532a13472a925e12c2373f6a55
Source dataset
uspto-grants-2008_03
Patent number
US07345067B2

Reaction notes

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