Sodium Bicarbonate → HCID 58487394, compound

HRID 874671Notes

Reaction equation

HRID 874671 reaction equation
[Br:1][C:2]1[C:3]([CH3:14])=[CH:4][C:5]2[O:9][C:8](C(O)=O)=[CH:7][C:6]=2[CH:13]=1.[B-](F)(F)(F)[F:16].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1.C(=O)(O)[O-].[Na+]>O.CC(=O)OCC>[Br:1][C:2]1[C:3]([CH3:14])=[CH:4][C:5]2[O:9][C:8]([F:16])=[CH:7][C:6]=2[CH:13]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724933Selectfluor2×HCID 671269275-Bromo-6-methylbenzofuran-2-carboxylic acid

Product 1

HCID 58487394HCID 58487394, compoundYield 36.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of 5-bromo-6-methyl-benzofuran-2-carboxylic acid (229, 243 mg, 0.95 mmol), Selectfluor (481 mg, 1.36 mmol) and sodium bicarbonate (228 mg, 2.72 mmol) in 3 ml water and 3 ml EA was stirred vigorously at r.t. for 60 h before addition of another 240 mg of Selectfluor. After further 20 h the reaction mixture was diluted with EA, washed twice with 1N NaOH. Org phase was washed with brine, dried over sodium sulfate, concentrated to dryness to give 78.5 mg of title compound as light brown wax (yield: 36.1%, purity>95%).

Workup

  1. washwashed twice with 1N NaOH
  2. washOrg phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-80082744764f4dd183d3ef152e95bdb5
Source dataset
uspto-grants-2015_03
Patent number
US08980629B2

Reaction notes

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