Hydrogen Bromide → HCID 20137577, compound

HRID 1253312Notes

Reaction equation

HRID 1253312 reaction equation
[Br:1][CH:2]([C:4]1([C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:23][CH3:24])[C:18]=3Br)[CH:13]=2)[O:9][CH2:8][C:7]([CH3:11])([CH3:10])[CH2:6][O:5]1)[CH3:3].[N+](C1C=CC=CC=1)([O-])=O.Br.C1(O)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[Br:1][CH:2]([C:4]1([C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:23][CH3:24])[CH:18]=3)[CH:13]=2)[O:5][CH2:6][C:7]([CH3:11])([CH3:10])[CH2:8][O:9]1)[CH3:3]

Participants

7

Reactant 5

HCID 260Hydrogen BromideHCID 996PhenolHCID 7416NitrobenzeneHCID 10340Sodium CarbonateHCID 20137579HCID 20137579, compound

Product 1

HCID 20137577HCID 20137577, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-(1-bromoethyl)-2-(5-bromo-6-methoxy-2-naphthyl)-5,5-dimethyl-1,3-dioxane (9.16 g, 10 mmol) is dissolved in toluene (40 ml) and nitrobenzene (2 g) saturated with HBr at room temperature. Phenol (11.28 g, 120 mmol) is added as solid; the mixture is stirred for 2.5 hours, then is poured in 30 minutes under stirring into a 10% aqueous sodium carbonate solution (150 ml), the organic layer is separated and the aqueous phase is extracted with toluene. The combined organic extracts are washed with water, dried on sodium sulphate and the solvent is removed in vacuo. 2-(1-bromoethyl)-2-(6-methoxy-2-naphthyl)-5,5-dimethyl-1,3-dioxane is obtained (75% yield).

Workup

  1. customat room temperature
  2. additionis poured in 30 minutes
  3. customthe organic layer is separated
  4. extractionthe aqueous phase is extracted with toluene
  5. washThe combined organic extracts are washed with water
  6. customdried on sodium sulphate
  7. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-e5a6a8855d8a44eeb3c59bbaeea10f88
Source dataset
uspto-grants-1988_05
Patent number
US04748256

Reaction notes

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