Potassium Carbonate → Tert-butyl (4'-formylbiphenyl-3-ylmethyl)methylcarbamate

HRID 1072101Notes

Reaction equation

HRID 1072101 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][N:6]([CH3:14])[C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].[CH:18]([C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1)=[O:19].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[CH:18]([C:20]1[CH:25]=[CH:24][C:23]([C:2]2[CH:17]=[CH:16][CH:15]=[C:4]([CH2:5][N:6]([CH3:14])[C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH:3]=2)=[CH:22][CH:21]=1)=[O:19]

Participants

5

Reactant 3

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

Product 1

HCID 86591268Tert-butyl (4'-formylbiphenyl-3-ylmethyl)methylcarbamate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

61.5 g (205 mmol) of tert-butyl (3-bromobenzyl)-N-methylcarbamate, 40 g (260 mmol) of 4-formylbenzeneboronic acid and 800 ml of toluene are introduced into a three-necked flask and under argon. 205 ml of an aqueous potassium carbonate solution (2 M) are added dropwise, the reaction medium is degassed with argon and 7 g of tetrakis(triphenylphosphine)-palladium(0) chloride are added and the mixture is heated at 90° C. for 24 hours. The reaction medium is poured into water, extracted with dichloromethane, the organic phase decanted off, dried over magnesium sulphate and evaporated off. The residue obtained is purified by chromatography on a silica column eluted with a heptane and ethyl acetate (70-30) mixture. After evaporation of the solvents, 38 g (57%) of the expected product are recovered.

Workup

  1. customthe reaction medium is degassed with argon and 7 g of tetrakis(triphenylphosphine)-palladium(0) chloride
  2. additionare added
  3. additionThe reaction medium is poured into water
  4. extractionextracted with dichloromethane
  5. customthe organic phase decanted off
  6. dry with materialdried over magnesium sulphate
  7. customevaporated off
  8. customThe residue obtained
  9. customis purified by chromatography on a silica column
  10. washeluted with a heptane and ethyl acetate (70-30) mixture
  11. customAfter evaporation of the solvents, 38 g (57%) of the expected product
  12. customare recovered

Sources & evidence

ORD record
ord-4e26985e99ba46bc9404197c15a11ec9
Source dataset
uspto-grants-2005_06
Patent number
US06908939B2

Reaction notes

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