Ethyl bromoacetate → HCID 59741469, compound

HRID 1669626Notes

Reaction equation

HRID 1669626 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34]>CN(C=O)C.C(OCC)(=O)C>[C:20]([O:19][C:18]([NH:17][CH:12]([C:8]1([C:5]2[CH:6]=[CH:7][C:2]([O:1][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:3][CH:4]=2)[CH2:9][CH2:10][CH2:11]1)[CH2:13][CH:14]([CH3:16])[CH3:15])=[O:24])([CH3:22])([CH3:21])[CH3:23]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 59741478HCID 59741478, compound

Product 1

HCID 59741469HCID 59741469, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of phenol 67 (0.5 g, 0.0015 mole) in 25 mL of anhydrous DMF was added cesium carbonate (Cs2CO3). The resulting mixture was heated at 70° C. for 12 hours. The reaction mixture was cooled to room temperature and added ethyl bromoacetate. The reaction mixture was further stirred at 70° C. for 8 hours and the progress of the reaction was monitored by TLC. The reaction mixture was diluted with ethyl acetate (100 mL), washed with water (50 mL×2), dried over anhydrous sodium sulfate (Na2SO4) and evaporated. The residue was purified by silica gel column chromatography using 0-50% gradient of ethyl acetate and hexane as eluent to give the pure ester 69 as colorless liquid in 61% (0.38 g) yield. MS (ESI): m/z=420.00 (M+H+).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with water (50 mL×2)
  3. dry with materialdried over anhydrous sodium sulfate (Na2SO4)
  4. customevaporated
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dae9d8d7e0bc4a20b8ce590baf9247ff
Source dataset
uspto-grants-2011_08
Patent number
US07989500B2

Reaction notes

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