Methanol → 1-Methoxy-4-(trifluoromethyl)benzene

HRID 1767620Notes

Reaction equation

HRID 1767620 reaction equation
[Na].Br[C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][CH:4]=1.[CH3:13][OH:14]>>[F:10][C:9]([F:12])([F:11])[C:6]1[CH:7]=[CH:8][C:3]([O:14][CH3:13])=[CH:4][CH:5]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-HCID 5360545Sodium

Product 1

HCID 6006041-Methoxy-4-(trifluoromethyl)benzeneYield 41%

Conditions

Temperature
130 °C

Procedure

Sodium (12.78 g; 555 mmol) was added to dry MeOH (100 ml). When the gas evolution ceased, the reaction mixture was evaporated to dryness and dry NMP (250 ml) followed by Cu (s) (35.3; 555 mmol) and 4-bromo-trifluoromethylbenzene (25 g; 111 mmol) was added. The reaction mixture was heated to 130° C. for 4 h, cooled to rt. and filtered. Water (500 ml) was added to the filtrate and it was extracted with Et2O (2×200 ml). The combined organic fractions were washed with H2O (2×100 ml), dried (MgSO4) and evaporated to dryness. Column chromatography gave 8.05 g (41%) of product.

Workup

  1. customthe reaction mixture was evaporated to dryness and dry NMP (250 ml)
  2. additionwas added
  3. temperaturecooled to rt
  4. filtrationand filtered
  5. additionWater (500 ml) was added to the filtrate and it
  6. extractionwas extracted with Et2O (2×200 ml)
  7. washThe combined organic fractions were washed with H2O (2×100 ml)
  8. dry with materialdried (MgSO4)
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-508a1c131d8d4e469b4b2e4dfc6b822e
Source dataset
uspto-grants-2007_06
Patent number
US07235548B2

Reaction notes

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