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

HRID 249724

Reaction equation

HRID 249724 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 (6.8 g) was dissolved in absolute methanol (50 ml) and treated successively with DL-10-camphorsulfonic acid (111 mg) and trimethyl orthoformate (8 ml). After stirring at RT for 2 h, DMF (75 ml) and potassium carbonate (5.0 g) were added, followed by iodomethane (3 ml). After stirring for 6 h, the batch was allowed to stand overnight and was treated with a 1:1 mixture of n-heptane/water. After separating off the organic phase, it was additionally extracted once with n-heptane and then the combined heptane phases were dried over magnesium sulfate, filtered and concentrated. 7 g of the desired product were obtained.

Workup

  1. stirringAfter stirring for 6 h
  2. waitto stand overnight
  3. customAfter separating off the organic phase, it
  4. extractionwas additionally extracted once with n-heptane
  5. dry with materialthe combined heptane phases were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d7babac152f64052b75fdb5119acece3
Source dataset
uspto-grants-2011_01
Patent number
US07863269B2

Linked notes

Loading…