Methyl iodide → 1-Bromo-5-(1,1-dimethoxyethyl)-2-methoxy-3-trifluoromethylbenzene

HRID 657982

Reaction equation

HRID 657982 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](C(=O)C)[CH:5]=[C:6]([C:9]([F:12])([F:11])[F:10])[C:7]=1O.[CH:16]([O:21][CH3:22])([O:19][CH3:20])OC.[C:23](=[O:26])([O-])[O-].[K+].[K+].I[CH3:30]>CO.CC1(C)[C@]2(CS(O)(=O)=O)C(C[C@H]1CC2)=O.CCCCCCC.O.CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:16]([O:19][CH3:20])([O:21][CH3:22])[CH3:30])[CH:5]=[C:6]([C:9]([F:10])([F:11])[F:12])[C:7]=1[O:26][CH3:23]

Participants

9

Reactant 4

HCID 6328Methyl iodideHCID 9005Trimethyl orthoformateHCID 11430Potassium CarbonateHCID 580857003'-Bromo-4'-hydroxy-5'-(trifluoromethyl)acetophenone

Product 1

HCID 580856971-Bromo-5-(1,1-dimethoxyethyl)-2-methoxy-3-trifluoromethylbenzene

Reagents, catalysts & solvents 4

HCID 65617D-Camphorsulfonic AcidCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 57468513Heptane waterSolvent

Procedure

1-(3-Bromo-4-hydroxy-5-trifluoromethylphenyl)ethanone (O4.004; 6.8 g) was dissolved in methanol (50 ml) and admixed successively with DL-10-camphorsulfonic acid (111 mg) and trimethyl orthoformate (8 ml). After stirring at RT for 2 h, DMF (75 ml), potassium carbonate (4.98 g) and then slowly, while cooling with ice, iodomethane (3 ml) were added. After stirring at RT for 4 h, the reaction mixture was left to stand overnight and then admixed with n-heptane/water, and the organic phase was removed. The aqueous phase was extracted by shaking once more with n-heptane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. 7 g of the title compound were obtained in sufficient purity.

Workup

  1. additionwere added
  2. stirringAfter stirring at RT for 4 h
  3. waitthe reaction mixture was left
  4. waitto stand overnight
  5. customthe organic phase was removed
  6. extractionThe aqueous phase was extracted
  7. stirringby shaking once more with n-heptane
  8. dry with materialthe combined organic phases were then dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-5992c9e592904eba8876e241466c6e2e
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Linked notes

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