Benzyl Bromide → Benzyl 4-bromo-2-fluorobenzoate

HRID 1177102Notes

Reaction equation

HRID 1177102 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:9][C:10]1[CH:18]=[C:17]([Br:19])[CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=[O:13].C([O-])([O-])=O.[Cs+].[Cs+]>C(Cl)Cl>[CH2:1]([O:14][C:12](=[O:13])[C:11]1[CH:15]=[CH:16][C:17]([Br:19])=[CH:18][C:10]=1[F:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 3026814-Bromo-2-fluorobenzoic acid

Product 1

HCID 22351348Benzyl 4-bromo-2-fluorobenzoateYield 102.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyl bromide (2.80 mL, 23.6 mmol) was added to a solution of 2-fluoro-4-bromobenzoic acid (4.34 g, 19.8 mmol) and Cs2CO3 (9.79 g, 30.0 mmol) in CH2Cl2 (50 mL). The mixture was heated to reflux for 4 hr. The reaction was quenched with H2O (150 mL) and extracted with CH2Cl2 (150 mL). The organic layer was dried over MgSO4 and concentrated. The residue was purified by flash column chromatograph eluting with 10% EtOAc in hexanes to give a colorless oil (6.27 g, 100% yield). 1H NMR (400 MHz, CDCl3) δ 7.82-7.88 (m, 1 H) 7.44-7.47 (m, 2 H) 7.34-7.42 (m, 5 H) 5.38 (s, 2 H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 hr
  3. customThe reaction was quenched with H2O (150 mL)
  4. extractionextracted with CH2Cl2 (150 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatograph
  8. washeluting with 10% EtOAc in hexanes

Sources & evidence

ORD record
ord-8e1724e573464eb9bdb4a5910a32cc5a
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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