Methanol → Benzoic acid, 4-amino-2,3-difluoro-5-nitro-, methyl ester

HRID 216999Notes

Reaction equation

HRID 216999 reaction equation
[Si](C=[N+]=[N-])(C)(C)[CH3:2].[NH2:8][C:9]1[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[C:11]([F:21])[C:10]=1[F:22].CO>C1COCC1>[CH3:2][O:14][C:13](=[O:15])[C:12]1[CH:16]=[C:17]([N+:18]([O-:20])=[O:19])[C:9]([NH2:8])=[C:10]([F:22])[C:11]=1[F:21]

Participants

5

Reactant 3

HCID 887MethanolHCID 167693TrimethylsilyldiazomethaneHCID 162440884-Amino-2,3-difluoro-5-nitrobenzoic acid

Product 1

HCID 2759749Benzoic acid, 4-amino-2,3-difluoro-5-nitro-, methyl esterYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 2 M solution of TMS diazomethane in hexanes (6.88 mL, 13.75 mmol) is added to a suspension of 4-amino-2,3-difluoro-5-nitro-benzoic acid 3 (2.00 g, 9.17 mmol) in 25 mL of 4:1 THF:MeOH at 0° C. under nitrogen atmosphere. Upon completion of addition, reaction mixture is warmed to room temperature. After 0.5 hours, excess TMS diazomethane is destroyed by the careful addition of acetic acid. The reaction is then concentrated under reduced pressure and dried in vacuo to give 1.95 g (92%) of pure desired product: MS APCI (−) m/z 231 (M−1) detected.

Workup

  1. customat 0° C.
  2. additionUpon completion of addition, reaction mixture
  3. customexcess TMS diazomethane is destroyed by the careful addition of acetic acid
  4. concentrationThe reaction is then concentrated under reduced pressure
  5. customdried in vacuo

Sources & evidence

ORD record
ord-9164d19235444975b55592903f6f50f1
Source dataset
uspto-grants-2012_06
Patent number
US08193231B2

Reaction notes

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