Potassium Phosphate, Tribasic → HCID 86687719, compound

HRID 1473647Notes

Reaction equation

HRID 1473647 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1B(O)O.[Br:12][C:13]1[CH:14]=[CH:15][C:16]([CH:23]=[O:24])=[C:17]([CH:22]=1)[C:18]([O:20]C)=O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1CC=CCCC=C1.C1CC=CCCC=C1.[Cl-].[Cl-].[Rh].[Rh].C1COCC1>[Br:12][C:13]1[CH:22]=[C:17]2[C:16]([CH:23]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])[O:24][C:18]2=[O:20])=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27339582-Methoxyphenylboronic acidHCID 53419722Methyl 5-bromo-2-formylbenzoate2×

Product 1

HCID 86687719HCID 86687719, compoundYield 78.3%

Reagents, catalysts & solvents 2

HCID 6436379Rhodium, di-mu-chlorobis((1,2,5,6-eta)-1,5-cyclooctadiene)di-CatalystHCID 8028TetrahydrofuranSolvent

Procedure

(2-Methoxyphenyl)boronic acid (4.69 g, 30.9 mmol), methyl 5-bromo-2-formylbenzoate (5.00 g, 20.6 mmol; GLSyntech, LLC), tripotassium phosphate (17.5 g, 82.0 mmol) and THF (103 mL) were added to a pressure tube. The tube was purged with argon. Then chloro(1,5-cyclooctadiene)rhodium(I) dimer (0.507 g, 1.03 mmol) was added. The tube was sealed and stirred at rt. After 30 min, LCMS showed lactone product. TLC confirmed a complete conversion of methyl 5-bromo-2-formylbenzoate to a lower spot. The reaction was filtered with the aid of EtOAc. The filtrate was concentrated and the crude material was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (120 g), eluting with a gradient of 0% to 30% EtOAc in hexanes, to provide 6-bromo-3-(2-methoxyphenyl)isobenzofuran-1(3H)-one (5.15 g, 78% yield). m/z (ESI) 319.0 (M+H)+, 321.0 (M+3H)+.

Workup

  1. customThe tube was purged with argon
  2. customThe tube was sealed
  3. filtrationThe reaction was filtered with the aid of EtOAc
  4. concentrationThe filtrate was concentrated
  5. customthe crude material was absorbed onto a plug of silica gel
  6. custompurified by chromatography through a Redi-Sep pre-packed silica gel column (120 g)
  7. washeluting with a gradient of 0% to 30% EtOAc in hexanes

Sources & evidence

ORD record
ord-eb3e2e61e3234f84bc027dae9f3d5e74
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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