Water → HCID 21255622, compound

HRID 636762Notes

Reaction equation

HRID 636762 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([CH:29]=[CH:30][C:31]=3[O:32][CH3:33])[C:14]([CH2:16][O:17][C:18]3[CH:19]=[C:20]([CH:25]=[CH:26][C:27]=3[CH3:28])[C:21]([O:23][CH3:24])=[O:22])=[O:15])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:52]N1C(=O)CCC1=O.O>C(Cl)(Cl)(Cl)Cl.ClCCl>[C:1]12([C:11]3[CH:12]=[C:13]([CH:29]=[CH:30][C:31]=3[O:32][CH3:33])[C:14]([CH2:16][O:17][C:18]3[CH:19]=[C:20]([CH:25]=[CH:26][C:27]=3[CH2:28][Br:52])[C:21]([O:23][CH3:24])=[O:22])=[O:15])[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Participants

7

Reactant 4

HCID 962WaterHCID 7187Benzoyl Peroxide2×HCID 67184N-bromobutanimideHCID 21255609HCID 21255609, compound

Product 1

HCID 21255622HCID 21255622, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 3[(3-(1-adamantyl)-4-methoxybenzoyl)methyloxy]-4-methylbenzoate (2.36 g, 5.26 mmol) and benzoyl peroxide (0.02 g) in carbon tetrachloride (50 ml) was heated to reflux. Benzoyl peroxide (0.03 g) and N-bromosuccinimide (1.05 g, 5.9 mmol) were added. The mixture was heated for four hours at reflux. 50 ml of water and 50 ml of dichloromethane were added. After separation of the phases once settling had taken place, the organic phase was washed twice with 50 ml of water and dried over magnesium sulfate. After concentration on a rotary evaporator at 40° C. under vacuum, the desired product was isolated by flash chromatography (CH2Cl2). Its properties were as follows:

Workup

  1. temperatureThe mixture was heated for four hours
  2. temperatureat reflux
  3. customAfter separation of the phases
  4. washthe organic phase was washed twice with 50 ml of water
  5. dry with materialdried over magnesium sulfate
  6. concentrationAfter concentration
  7. customon a rotary evaporator at 40° C. under vacuum

Sources & evidence

ORD record
ord-fdb5eb2eded94999bc6aa0edc5ec33fb
Source dataset
uspto-grants-2001_02
Patent number
US06194450B1

Reaction notes

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