Hexane → Methyl 5-bromo-2-(2-fluorophenylamino)-3,4-difluorobenzoate

HRID 558243Notes

Reaction equation

HRID 558243 reaction equation
[Br:1][C:2]1[C:3]([F:20])=[C:4]([F:19])[C:5]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[Si](C=[N+]=[N-])(C)(C)[CH3:22].CCCCCC>C1COCC1.CO>[Br:1][C:2]1[C:3]([F:20])=[C:4]([F:19])[C:5]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:22])=[O:8]

Participants

5

Reactant 3

HCID 8058HexaneHCID 167693TrimethylsilyldiazomethaneHCID 595193885-Bromo-3,4-difluoro-2-((2-fluorophenyl)amino)benzoic acid

Product 1

HCID 59519391Methyl 5-bromo-2-(2-fluorophenylamino)-3,4-difluorobenzoateYield 96%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 5-bromo-2-(2-fluorophenylamino)-3,4-difluorobenzoic acid (30.3 mmol, 11 g) in THF:MeOH (60:20), cooled to 0° C., was added dropwise a solution of 2M TMSCHN2 in hexane (39.39 mmol, 19.7 ml). After the addition is completed, the reaction mixture was warmed to room temperature and stirred for an additional 4 hours. The crude reaction was quenched with acetic acid and extracted with EtOAc. The organic layers are combined, washed with H2O, dry over MgSO4 and concentrated under reduced pressure. The crude material was dried under vacuum and yields to 11 g (96%) of the title product.

Workup

  1. additionAfter the addition
  2. customThe crude reaction
  3. customwas quenched with acetic acid
  4. extractionextracted with EtOAc
  5. washwashed with H2O
  6. dry with materialdry over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. dry with materialThe crude material was dried under vacuum

Sources & evidence

ORD record
ord-3ade5f9496bb432a814e32d597a3339b
Source dataset
uspto-grants-2011_11
Patent number
US08063049B2

Reaction notes

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