HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Sodium Carbonate → (1,1'-Biphenyl)-2-carboxaldehyde

HRID 334258
Notes
Print preview

Reaction equation

HRID 334258 reaction equation
Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C)C=O.CCOC(C)=O.C([O-])(O)=O.[Na+].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>[C:2]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:3]([CH:4]=[O:5])=[CH:6][CH:7]=[CH:8][CH:9]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 811292-Bromobenzaldehyde

Product 1

HCID 121052(1,1'-Biphenyl)-2-carboxaldehydeYield 75.2%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalyst
HCID 6228
Dimethylformamide
Solvent
HCID 8857Ethyl AcetateSolvent
HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
160 °C

Procedure

2-Bromobenzaldehyde (315 μL, 2.70 mmol), phenylboronic acid (395 mg, 3.24 mmol), Pd(PPh3)4 (31 mg, 0.027 mmol) and Na2CO3 (430 mg, 4.05 mmol) were dissolved in N,N-dimethylformamide (20 mL) in a reaction vessel and refluxed at 160° C. for 6 hours. After the reaction was completed, the reaction mixture was diluted with EtOAc and saturated NaHCO3 solution was added. The organic layer obtained by extracting the aqueous layer with EtOAc was dried with anhydrous MgSO4 and then filtered. The filtrate was concentrated under reduced pressure and the concentrate was purified by column chromatography (hexane:diethyl ether=8:1) to obtain 369 mg of the target compound (2.03 mmol, 75.0%).

Workup

  1. additionwas added
  2. customThe organic layer obtained
  3. extractionby extracting the aqueous layer with EtOAc
  4. dry with materialwas dried with anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe concentrate was purified by column chromatography (hexane:diethyl ether=8:1)

Sources & evidence

ORD record
ord-cf70e14551404b549f65d855c83a2831
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08883796B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes