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

HRID 733388Notes

Reaction equation

HRID 733388 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 acid2×

Product 1

HCID 2316083-Bromo-9H-xanthen-9-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-bromo-2-phenoxybenzoic acid, 2a (35.1 g, 120 mmol) in. methylene chloride (350 mL) at 0° C. was added dropwise trifluoroacetic anhydride (20.3 mL, 144 mmol), and the reaction was stirred for 15 min. Boron trifluoride diethyl etherate (1.46 mL, 12.0 mmol) was added dropwise. The reaction became homogeneous upon stirring for 1 h at rt. The reaction was poured into 1 N NaOH, and the organic phase was dried over magnesium sulfate, filtered, and concentrated to give title compound 3-bromo-xanthen-9-one, 3a (32.14 g, 116 mmol). MS m/z (MH+) 275.

Workup

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

Sources & evidence

ORD record
ord-a8db1f781613451da930e42b96089815
Source dataset
uspto-grants-2009_09
Patent number
US07589104B2

Reaction notes

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