Benzyl Bromide → Ethyl 2-(4-(benzyloxy)-3-bromophenyl)acetate

HRID 563662Notes

Reaction equation

HRID 563662 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([Br:13])[CH:7]=1)[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CC#N>[CH2:1]([O:3][C:4](=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:8]([Br:13])[CH:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 18620106Ethyl 2-(3-bromo-4-hydroxyphenyl)acetate

Product 1

HCID 18620085Ethyl 2-(4-(benzyloxy)-3-bromophenyl)acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of (3-bromo-4-hydroxy-phenyl)-acetic acid ethyl ester (0.100 g, 0.39 mmol) and cesium carbonate (0.376 g, 1.16 mmol) in MeCN was added benzyl bromide (0.06 mL, 0.46 mmol), and the reaction was stirred at room temperature until no starting material was seen by analytical tlc. The mixture was partitioned between EtOAc and H2O, and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated to give the title compound.

Workup

  1. customThe mixture was partitioned between EtOAc and H2O
  2. extractionthe aqueous layer was extracted with EtOAc
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3a0aa6086fd9412c80c875c8103a2250
Source dataset
uspto-grants-2011_11
Patent number
US08067445B2

Reaction notes

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