Toluene → HCID 86761347, compound

HRID 1009217Notes

Reaction equation

HRID 1009217 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[C:8]1[CH:9]=[C:10]([CH:21]=[CH:22][CH:23]=1)[CH2:11][N:12](C)[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].[CH:24]([C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1)=[O:25].C1(C)C=CC=CC=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH:24]([C:26]1[CH:31]=[CH:30][C:29]([C:8]2[CH:23]=[CH:22][CH:21]=[C:10]([CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH:9]=2)=[CH:28][CH:27]=1)=[O:25]

Participants

7

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 20738487tert-Butyl 3-bromobenzyl(methyl)carbamate

Product 1

HCID 86761347HCID 86761347, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

307 ml (615 mmol) of an aqueous potassium carbonate solution (2M) are added dropwise to a mixture of 61.5 g (205 mmol) of tert-butyl (3-bromobenzyl)-N-methylcarbamate, 46 g (307 mmol) of 4-formylbenzeneboronic acid and 500 ml of toluene. The reaction medium is subsequently degassed with argon and 7 g (6.2 mmol) of tetrakis(triphenylphosphine)palladium(0) are added. After heating at 90° C. for 24 hours, the reaction medium is poured into water and extracted with ethyl acetate. The organic phase is separated by settling, dried over magnesium sulfate and evaporated. The residue obtained is purified by chromatography on a silica column eluted with a mixture of heptane and ethyl acetate (70/30). After evaporating the solvents, 67 g of tert-butyl (4′-formylbiphenyl-3-yl)methylcarbamate are collected. Yield=60%.

Workup

  1. additionare added
  2. extractionextracted with ethyl acetate
  3. customThe organic phase is separated
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by chromatography on a silica column
  8. washeluted with a mixture of heptane and ethyl acetate (70/30)
  9. customAfter evaporating the solvents, 67 g of tert-butyl (4′-formylbiphenyl-3-yl)methylcarbamate
  10. customare collected

Sources & evidence

ORD record
ord-fc4a8753e3394cbab353bc6d433f2439
Source dataset
uspto-grants-2011_07
Patent number
US07973063B2

Reaction notes

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