Tetrahydrofuran → HCID 86758993, compound

HRID 1368031Notes

Reaction equation

HRID 1368031 reaction equation
[C:1]([O:5][C:6]1[CH:7]=[C:8]([N:16]=[C:17]=[O:18])[C:9]([OH:15])=[C:10]([CH:14]=1)[C:11]([OH:13])=[O:12])([CH3:4])([CH3:3])[CH3:2].O1[CH2:23][CH2:22][CH2:21][CH2:20]1.C(Br)(Br)(Br)[Br:25]>>[Br:25][CH2:20][CH2:21][CH2:22][CH2:23][O:12][C:11](=[O:13])[C:10]1[CH:14]=[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH:7]=[C:8]([N:16]=[C:17]=[O:18])[C:9]=1[OH:15]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 11205Carbon tetrabromideHCID 86758994HCID 86758994, compound

Product 1

HCID 86758993HCID 86758993, compound

Procedure

To a solution of 5-tertbutyloxy-carbonylamino-2-hydroxy-benzoic acid (20 g, 85.7 mmoles) in tetrahydrofuran (200 ml) triphenylphosphine (44.9 g, 171 mmoles) and lastly carbon tetrabromide (56.7 g, 171 mmoles) are added. The reaction mixture is left under stirring at room temperature for 24 hours and then evaporated under vacuum. The obtained residue is purified by silica gel column chromatography (eluent: n.-hexane/ethyl acetate 8/2 vol./vol.), monitoring the content of the collected fractions by chromatography on thin layer. The product is obtained by collecting the head fractions, after elution from the column of the CBr4 reactive used in the synthesis. The fractions are collected and dried. A white solid (21.16 mg) having m.p. 108°-111° C. is recovered.

Workup

  1. waitThe reaction mixture is left
  2. customevaporated under vacuum
  3. customThe obtained residue is purified by silica gel column chromatography (eluent: n.-hexane/ethyl acetate 8/2 vol./vol.)
  4. customThe product is obtained
  5. customby collecting the head fractions
  6. washafter elution from the column of the CBr4
  7. customreactive used in the synthesis
  8. customThe fractions are collected
  9. customdried
  10. customis recovered

Sources & evidence

ORD record
ord-2e2bf571b7134d4e8bec2629607f0467
Source dataset
uspto-grants-2003_06
Patent number
US06573252B1

Reaction notes

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