tert-Butyl acetate → HCID 20315612, compound

HRID 2419362Notes

Reaction equation

HRID 2419362 reaction equation
[Br:1]Br.[C:3]([C:6]1[CH:23]=[CH:22][C:9]([O:10][CH:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][CH:7]=1)(=[O:5])[CH3:4].C(OC(C)(C)C)(=O)C>C1C=CC=CC=1>[Br:1][CH2:4][C:3]([C:6]1[CH:23]=[CH:22][C:9]([O:10][CH:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][CH:7]=1)=[O:5]

Participants

5

Reactant 3

HCID 10908tert-Butyl acetateHCID 24408BromineHCID 20315551HCID 20315551, compound

Product 1

HCID 20315612HCID 20315612, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of bromine (5.4g.) in benzene (50ml.) was added dropwise over 1 hour to a stirred solution of diethyl 4-acetylphenoxymalonate (10.0g.) and t-butyl acetate (3.95g.) in benzene (200ml.). The solution was stirred for 30 minutes, washed with N-sodium bicarbonate solution (1 × 30ml.), water (3 × 40ml.), dried and evaporated. The residue was chromatographed on silica to give diethyl 4-(bromoacetyl)phenoxymalonate, m.p. 55°-58° C.

Workup

  1. washwashed with N-sodium bicarbonate solution (1 × 30ml.), water (3 × 40ml.)
  2. customdried
  3. customevaporated
  4. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-696df5f9c5b34f28a3ff5c3010519d13
Source dataset
uspto-grants-1978_08
Patent number
US04105790

Reaction notes

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