Methanol → HCID 15480130, compound

HRID 1872774Notes

Reaction equation

HRID 1872774 reaction equation
[CH3:1][C:2]1[C:3]([N+:17]([O-:19])=[O:18])=[C:4]([O:15]C)[CH:5]=[CH:6][C:7]=1[NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11].B(Br)(Br)Br.CO.O>C(Cl)Cl>[CH3:1][C:2]1[C:3]([N+:17]([O-:19])=[O:18])=[C:4]([OH:15])[CH:5]=[CH:6][C:7]=1[NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 25134Boron tribromideHCID 15480129HCID 15480129, compound

Product 1

HCID 15480130HCID 15480130, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 3-methyl-2-nitro4-trifluoroacetamidoanisole (5.37 g, 19.3 mmol) in dry methylene chloride (250 mL) at -78° C. under nitrogen atmosphere is treated dropwise with a solution of boron tribromide (9.16 mL, 96.9 mmol) in dry methylene chloride (50 mL). After complete addition, the mixture is allowed to warm to room temperature and stirring is maintained for one hour. The mixture is cooled to -78° C. and methanol (100 mL) is added dropwise. After complete addition, the solution is allowed to warm to room temperature. The reaction mixture is distributed between water (100 mL) and methylene chloride (200 mL). The methylene chloride layer is dried over magnesium sulfate and concentrated under reduced pressure to yield 4.81 g of 3-methyl-2-nitro-4-trifluoroacetamidophenol.

Workup

  1. additionAfter complete addition
  2. temperatureis maintained for one hour
  3. temperatureThe mixture is cooled to -78° C.
  4. additionAfter complete addition
  5. temperatureto warm to room temperature
  6. dry with materialThe methylene chloride layer is dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4ac5acb7c2f34ce79abc9b2441e399c9
Source dataset
uspto-grants-2000_08
Patent number
US06110952

Reaction notes

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