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

HRID 733047Notes

Reaction equation

HRID 733047 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-875eab9e6cd74fc7af06c24e010acd41
Source dataset
uspto-grants-2009_09
Patent number
US07589103B2

Reaction notes

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