Pivalic acid → HCID 66690849, compound

HRID 592311Notes

Reaction equation

HRID 592311 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Br:13])[C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].[CH3:14][C:15]([CH3:20])([CH3:19])[C:16](O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.ClC(Cl)(Cl)C#N>C(#N)C>[Br:13][C:10]1[C:11]2[O:12][C:14]([C:15]([CH3:20])([CH3:19])[CH3:16])=[N:1][C:2]=2[CH:3]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:9]=1

Participants

6

Reactant 4

HCID 6417Pivalic acidHCID 11011TrichloroacetonitrileHCID 11776TriphenylphosphineHCID 66545110Methyl 3-amino-5-bromo-4-hydroxybenzoate

Product 1

HCID 66690849HCID 66690849, compoundYield 19.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of methyl 3-amino-5-bromo-4-hydroxybenzoate (2.00 g, 4.06 mmol, 50% purity), 2,2-dimethylpropanoic acid (0.83 g, 8.13 mmol), and solid support triphenylphosphine (75% by weight; 4.26 g, 12.2 mmol) in acetonitrile (20 mL) was added trichloroacetonitrile (815 μL, 8.13 mmol). The mixture was heated in a microwave reactor for 10 min at 150° C. The mixture was cooled to ambient temperature, filtered and concentrated. Purification by silica gel chromatography (100% hexanes→70% hexanes/ethyl acetate) gave the title compound (245 mg). LC-MS [M]=312.1.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customPurification by silica gel chromatography (100% hexanes→70% hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-cc081a99ccff4547a491279baeb58222
Source dataset
uspto-grants-2016_01
Patent number
US09238647B2

Reaction notes

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