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

HRID 1788228Notes

Reaction equation

HRID 1788228 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-884ce1a72a3a4d16bb93ead737c620d2
Source dataset
uspto-grants-2009_03
Patent number
US07511058B2

Reaction notes

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