3-Bromophenol → HCID 19389133, compound

HRID 902604Notes

Reaction equation

HRID 902604 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[Br:13][C:14]1[CH:15]=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=1.[Br:21][CH2:22][CH2:23][CH2:24]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Br:21][CH2:22][CH2:23][CH2:24][O:20][C:16]1[CH:15]=[C:14]([Br:13])[CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 115633-BromophenolHCID 11776TriphenylphosphineHCID 123083-Bromo-1-propanolHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 19389133HCID 19389133, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethylazodicarboxylate (0.77 g, 3.8 mmol) was added to solution of 3-bromophenol (0.50 g, 3.2 mmol), 3-bromopropanol (0.53 g, 3.8 mmol), triphenylphosphine (1.0 g, 3.8 mmol) and THF (10 mL). The solution was maintained at RT for 16 h and then concentrated in vacuo. The residue was partitioned between methylene chloride and 10% NaHCO3 aq. solution and layers separated. The aqueous layer was extracted with methylene chloride (2×10 mL). The organic layers were combined, dried (MgSO4) and concentrated in vacuo. The crude product was purified by flash column chromatography (100 g silica gel 60, 230-400 mesh, 9:1 hexane:ethyl acetate as eluent) to give 0.63 g (71%) of the title compound as a pale yellow liquid. MS (ESI) 293.0 [M+H]+.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between methylene chloride and 10% NaHCO3 aq. solution and layers
  3. customseparated
  4. extractionThe aqueous layer was extracted with methylene chloride (2×10 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash column chromatography (100 g silica gel 60, 230-400 mesh, 9:1 hexane:ethyl acetate as eluent)

Sources & evidence

ORD record
ord-ef7e7d9845e24a67aea7aaa3e37c1f41
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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