Bromide ion → HCID 57640544, compound

HRID 2111950Notes

Reaction equation

HRID 2111950 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][CH:11]([CH2:13][NH:14][C:15]([C:17]3[S:18][C:19]([Cl:22])=[CH:20][CH:21]=3)=[O:16])[O:10][N:9]=2)=[CH:4][CH:3]=1.[CH:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1B(O)O)=[O:24].C([O-])([O-])=O.[K+].[K+].[Br-]>COCCOCCOC.O.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>[CH:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][CH:11]([CH2:13][NH:14][C:15]([C:17]3[S:18][C:19]([Cl:22])=[CH:20][CH:21]=3)=[O:16])[O:10][N:9]=2)=[CH:4][CH:3]=1)=[O:24]

Participants

8

Reactant 4

HCID 259Bromide ionHCID 11430Potassium CarbonateHCID 2921892-Formylphenylboronic acidHCID 11582095HCID 11582095, compound

Product 1

HCID 57640544HCID 57640544, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8150DiglymeSolvent

Procedure

Aryl bromide (Example 1, 200 mg, 0.50 mmol), 2-formylphenylboronic acid (90 mg, 0.60 mmol) and K2CO3 (106 mg, 1.0 mmol) were diluted with diglyme (5 mL) and water (1 mL). The mixture was degassed for 3-5 min, then treated with Pd(PPh3)4 (58 mg, 0.05 mmol) and heated to 120° C. until all starting bromide was consumed as determined by HPLC. The resulting mixture was diluted with water, filtered and the remaining solids purified by silica gel chromatography (0-10% Ethyl acetate/dichloromethane) affording the desired biphenyl aldehyde as a white solid. MS found for C22H17ClN2O3S as (M+H)+ 425.4, 427.4.

Workup

  1. customThe mixture was degassed for 3-5 min
  2. customwas consumed
  3. additionThe resulting mixture was diluted with water
  4. filtrationfiltered
  5. customthe remaining solids purified by silica gel chromatography (0-10% Ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-5ad14474b434400eaa387d9b2736c49d
Source dataset
uspto-grants-2009_04
Patent number
US07521470B2

Reaction notes

Loading…