N-bromobutanimide → Ethyl 2-bromo-2-(3-fluorophenyl)acetate

HRID 1255004Notes

Reaction equation

HRID 1255004 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:6][CH:7]=1.C1C(=O)N([Br:21])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:21][CH:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1)[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 11735538Ethyl 2-(3-fluorophenyl)acetate

Product 1

HCID 20711243Ethyl 2-bromo-2-(3-fluorophenyl)acetateYield 54%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl 2-(3-fluorophenyl)acetate (I8) (10.1 g, 55.0 mmol) in CCl4 (250 mL), NBS (9.70 g, 55.0 mmol) is added and the mixture refluxed for 2 hours at 80° C. (LC-MS monitoring: complete conversion). The solvent is evaporated and the resulting crude is dissolved in DCM and purified by filtration on a silica bed in order to obtain 7.80 g of (I9) as a colorless oil (54% yield).

Workup

  1. customThe solvent is evaporated
  2. dissolutionthe resulting crude is dissolved in DCM
  3. filtrationpurified by filtration on a silica bed in order

Sources & evidence

ORD record
ord-d006a322946b4c80aa8118e9af0922fc
Source dataset
uspto-grants-2013_06
Patent number
US08455646B2

Reaction notes

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