Boron tribromide → HCID 57894169, compound

HRID 1822303Notes

Reaction equation

HRID 1822303 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[C:18]([O:20]C)[CH:17]=[C:16]([F:22])[CH:15]=2)=[CH:9][C:8]=1[CH3:23])[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[C:18]([OH:20])[CH:17]=[C:16]([F:22])[CH:15]=2)=[CH:9][C:8]=1[CH3:23])[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 57894216HCID 57894216, compound

Product 1

HCID 57894169HCID 57894169, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A −78° C. solution of 3-[4-(3-fluoro-5-methoxy-phenoxy)-2-methyl-phenyl]-propionic acid ethyl ester (0.715 g, 2.15 mmol) in dry CH2Cl2 (10 mL) is treated with a 1 M CH2Cl2 solution of boron tribromide (6.5 mL, 6.5 mmol). The mixture is warmed to 0° C. and stirred for 1 hour under N2. Upon completion, the mixture is poured into ice water and extracted with Et2O. The organic layer is dried (Na2SO4), and the solvent is removed in vacuo to afford crude product that is absorbed on silica gel and purified by flash chromatography using a gradient of 5/1 to 1/1 to hexanes/ethyl acetate to afford 0.558 g (81%) of the title compound. Rf=0.36 (2/1 hexanes/EtOAc). 1H NMR (400 MHz, CDCl3). MS (ES−) m/z mass calculated for C18H19O4F 318, found 317 (M−1, 100%).

Workup

  1. extractionextracted with Et2O
  2. dry with materialThe organic layer is dried (Na2SO4)
  3. customthe solvent is removed in vacuo
  4. customto afford crude product that
  5. customis absorbed on silica gel
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-5bb0fdceeec84eecb0d1953dfb5fc5e7
Source dataset
uspto-grants-2009_10
Patent number
US07608639B2

Reaction notes

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