Dimethylformamide → 6-Bromo-1,2,3,4-tetrahydro-7-methoxy-1,1,4,4-tetramethylnaphthalene

HRID 2417332Notes

Reaction equation

HRID 2417332 reaction equation
[Br:1][C:2]1[C:3](O)=[CH:4][C:5]2[CH:6]([CH3:15])[CH2:7][CH:8](C)[C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.CN([CH:20]=[O:21])C.[H-].[Na+].I[CH3:25]>O>[Br:1][C:2]1[C:3]([O:21][CH3:20])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:25])[CH2:7][CH2:8][C:9]([CH3:12])([CH3:13])[C:10]=2[CH:11]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 226346613-Bromo-2-hydroxy-5,6,7,8-tetrahydro-5,5,8,6-tetramethylnaphthalene

Product 1

HCID 107327466-Bromo-1,2,3,4-tetrahydro-7-methoxy-1,1,4,4-tetramethylnaphthalene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

7 g (24.7 mmol) of 3-bromo-2-hydroxy-5,6,7,8-tetrahydro-5,5,8,6-tetramethylnaphthalene and 40 ml of DMF are introduced into a three-necked flask under a stream of nitrogren. 890mg (29.6 mmol) of sodium hydride (80% in oil) are added portionwise and the mixture is stirred until the evolution of gas has ceased. 1.7 ml (27 mmol) of iodomethane are then added and the mixture is stirred at room temperature for one hour. The reaction medium is poured into water and extracted with ethyl ether, and the organic phase is separated out after settling has taken place, dried over magnesium sulphate and evaporated. 7.3 g (99%) of the expected product are collected in the for of an oil which crystallizes slowly. Melting point 77-8° C.

Workup

  1. stirringthe mixture is stirred at room temperature for one hour
  2. extractionextracted with ethyl ether
  3. customthe organic phase is separated out after settling
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. custom7.3 g (99%) of the expected product are collected in the for of an oil which
  7. customcrystallizes slowly

Sources & evidence

ORD record
ord-008e8bcc101a4b898d82a80b1c110083
Source dataset
uspto-grants-2004_11
Patent number
US06825360B1

Reaction notes

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