Hydrochloric Acid → HCID 54213334, compound

HRID 1956754Notes

Reaction equation

HRID 1956754 reaction equation
[Br:1][CH:2]([C:10](Cl)=[O:11])[CH2:3][CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7].[C:13]1([OH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(C(C)C)CC)(C)C.Cl>C(OCC)C>[Br:1][CH:2]([C:10]([O:19][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:11])[CH2:3][CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 996PhenolHCID 81531DiisopropylethylamineHCID 23203302HCID 23203302, compound

Product 1

HCID 54213334HCID 54213334, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of methyl 5-bromo-5-chloroformylpentanoate (2.57 g) in diethyl ether (15 ml) was added a mixture of phenol (0.94 g) and diisopropylethylamine (1.30 g) in diethyl ether (10 ml). The mixture was stirred at room temperature for 15 minutes and poured into ice water and diluted hydrochloric acid. The organic layer was washed with water, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel eluting with a mixture of n-hexane and ethyl acetate (5:1) to give methyl 5-bromo-5-phenoxycarbonylpentanoate as an oil (2.33 g).

Workup

  1. washThe organic layer was washed with water
  2. dry with materialdried over magnesium sulfate
  3. customevaporated
  4. customThe residue was chromatographed on silica gel eluting with a mixture of n-hexane and ethyl acetate (5:1)

Sources & evidence

ORD record
ord-2357569a6ff04995b1b293814151c341
Source dataset
uspto-grants-1998_07
Patent number
US05780633

Reaction notes

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