Trimethylsilyldiazomethane → HCID 86712698, compound

HRID 1779054Notes

Reaction equation

HRID 1779054 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[C:3]=1[CH2:12][C:13]([OH:15])=[O:14].[C:16]1(C)C=CC=CC=1.CO.C[Si](C=[N+]=[N-])(C)C>CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[C:3]=1[CH2:12][C:13]([O:15][CH3:16])=[O:14]

Participants

5

Reactant 3

HCID 167693TrimethylsilyldiazomethaneHCID 21867641Toluene methanolHCID 45933689HCID 45933689, compound

Product 1

HCID 86712698HCID 86712698, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-(2-bromo-6-(trifluoromethyl)phenyl)acetic acid (0.306 g, 1.08 mmol) in 4:1 toluene/MeOH (8 mL) was added trimethylsilyldiazomethane (2.0 M in Et2O; 0.80 mL, 1.6 mmol). The resulting mixture was stirred at room temperature for 20 hours before diluting with EtOAc (40 mL) and washing with saturated aqueous NaHCO3 (3×40 mL). The organics were passed through a phase separation cartridge then concentrated under reduced pressure to give the title compound A91 (0.293 g, 91%); 1H NMR (400 MHz, CDCl3) δ 7.80 (d, J=8.3 Hz, 1H), 7.65 (d, J=7.8 Hz, 1H), 7.29 (m, 1H), 4.04 (m, 2H), 3.72 (s, 3H).

Workup

  1. washwashing with saturated aqueous NaHCO3 (3×40 mL)
  2. customThe organics were passed through a phase separation cartridge
  3. concentrationthen concentrated under reduced pressure

Sources & evidence

ORD record
ord-812819126c834535b47ff7050448a362
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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