Formic Acid → 7-Bromo-2,3-dihydrobenzofuran-3-ol

HRID 1615457Notes

Reaction equation

HRID 1615457 reaction equation
C(N(CC)CC)C.C(O)=O.[Br:11][C:12]1[C:20]2[O:19][CH2:18][C:17](=[O:21])[C:16]=2[CH:15]=[CH:14][CH:13]=1.C(OCC)(=O)C>C(Cl)Cl.O>[Br:11][C:12]1[C:20]2[O:19][CH2:18][CH:17]([OH:21])[C:16]=2[CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 284Formic AcidHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 41378967-BROMO-3-BENZOFURANONE

Product 1

HCID 657210567-Bromo-2,3-dihydrobenzofuran-3-olYield 94.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.2 ml) was added to formic acid (63 ml), to the resultant mixture, a solution in methylene chloride (2.1 ml) of 7-bromo-2,3-dihydrobenzofuran-3-one (0.10 g) that is commercially available or can be obtained by a publicly known method was added, chloro[(1S,2S)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine]-(mesitylene) ruthenium (II) (8.8 mg) was added, and the resultant mixture was stirred at room temperature for 3 hours. To the resultant mixture, ethyl acetate and water were added, followed by extracting the resultant mixture with ethyl acetate, and the organic phase was washed with a saturated saline, and then was dried over anhydrous sodium sulfate. From the organic phase, the solvent was distilled off under reduced pressure, followed by purifying the resultant residue by silica gel column chromatography (eluate; n-hexane:ethyl acetate=5:1 to 3:1), and from the resultant, the solvent was distilled off under reduced pressure to obtain the subject compound (95 mg) as pale orange oil.

Workup

  1. customcan be obtained by a publicly known method
  2. additionwas added
  3. extractionby extracting the resultant mixture with ethyl acetate
  4. washthe organic phase was washed with a saturated saline
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. distillationFrom the organic phase, the solvent was distilled off under reduced pressure
  7. customby purifying the resultant residue by silica gel column chromatography (eluate; n-hexane:ethyl acetate=5:1 to 3:1)
  8. distillationfrom the resultant, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-cc4401614da44c3bbcb23bcc33b540ae
Source dataset
uspto-grants-2014_07
Patent number
US08765752B2

Reaction notes

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