Methanol → Methyl 4-amino-3-(trifluoromethoxy)benzoate

HRID 1830722Notes

Reaction equation

HRID 1830722 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[O:11][C:12]([F:15])([F:14])[F:13].CO.[Si](C=[N+]=[N-])(C)(C)[CH3:19].CCOC(C)=O.CCCCCC>C1COCC1>[CH3:19][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([NH2:1])=[C:3]([O:11][C:12]([F:13])([F:14])[F:15])[CH:4]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 167693TrimethylsilyldiazomethaneHCID 27359514-amino-3-(trifluoromethoxy)benzoic AcidHCID 21226206Ethyl acetate hexane

Product 1

HCID 53419671Methyl 4-amino-3-(trifluoromethoxy)benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-amino-3-trifluoromethoxy-benzoic acid (1.2 g, 5.4 mmol) in 16 mL of 4:1 THF:MeOH at 0 ° C. was added TMS -diazomethane (2M solution in hexane, 6 mL, 12 mmol) dropwise and conversion was monitored by TLC in ⅔ EtOAc/hexane. When complete, the reaction was concentrated to a white solid corresponding to the methyl ester (1.27 g, quantitative).

Workup

  1. concentrationWhen complete, the reaction was concentrated to a white solid corresponding to the methyl ester (1.27 g, quantitative)

Sources & evidence

ORD record
ord-16b9b872349641a0bebb682e6dc85df2
Source dataset
uspto-grants-2006_06
Patent number
US07067506B2

Reaction notes

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