Tetrahydrofuran → 5-Bromo-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid methyl ester

HRID 857494Notes

Reaction equation

HRID 857494 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[Cl:18])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH2:21]1COCC1.C[Si](C=[N+]=[N-])(C)C>CO>[CH3:21][O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([Br:1])[C:3]([F:20])=[C:4]([F:19])[C:5]=1[NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 167693TrimethylsilyldiazomethaneHCID 218669915-Bromo-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid

Product 1

HCID 865967715-Bromo-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid methyl esterYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-bromo-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid (3) (4.50 g, 12.4 mmol) in a 3:1 mixture of THF:MeOH (32 mL) was added (trimethylsilyl)-diazomethane (8.10 ml of a 2 M solution in hexanes) at room temperature. After stirring for 2 hours, the reaction mixture was quenched with acetic acid, diluted with EtOAc, and washed with water. The organic layer was dried (MgSO4) and concentrated under reduced pressure to give 4.35 g (93%) of the desired methyl ester (4).

Workup

  1. customthe reaction mixture was quenched with acetic acid
  2. additiondiluted with EtOAc
  3. washwashed with water
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d60222ee28894f39b480f23bbd912754
Source dataset
uspto-grants-2006_12
Patent number
US07144907B2

Reaction notes

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