Boron trifluoride etherate → 3-Bromo-9H-xanthen-9-one

HRID 425272Notes

Reaction equation

HRID 425272 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:3]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.B(F)(F)F.CCOCC.[OH-].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]2[C:6](=[O:8])[C:17]3[C:12]([O:11][C:4]=2[CH:3]=1)=[CH:13][CH:14]=[CH:15][CH:16]=3

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 9845Trifluoroacetic anhydrideHCID 14798Sodium HydroxideHCID 230539204-Bromo-2-phenoxybenzoic acid

Product 1

HCID 2316083-Bromo-9H-xanthen-9-oneYield 96.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-bromo-2-phenoxy-benzoic acid (35.1 g, 120 mmol) in CH2Cl2 (350 mL) at 0° C. was added trifluoroacetic anhydride (20.3 mL, 144 mmol), dropwise, and the reaction was stirred for 15 min. At that time, boron trifluoride diethyl etherate (1.46 mL, 12.0 mmol) was added, dropwise. The reaction became homogeneous upon stirring for 1 h at room temperature. Upon completion, the reaction was poured into 1 N NaOH, and the organic phase was dried over magnesium sulfate, filtered, and concentrated to give Compound 3a (32.14 g, 116 mmol). MS m/z (MH+) 275.

Workup

  1. stirringupon stirring for 1 h at room temperature
  2. dry with materialthe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7c50d6b1737843ad92a98d52f4561fec
Source dataset
uspto-grants-2012_01
Patent number
US08106207B2

Reaction notes

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