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

Sodium Carbonate → HCID 67973755, compound

HRID 1777536
Notes
Print preview

Reaction equation

HRID 1777536 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[F:13].[F:14][C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>O.COCCOC.C(OCC)(=O)C.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>[F:13][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:3]=1[CH2:2][C:19]1[CH:18]=[CH:17][CH:16]=[C:15]([F:14])[CH:20]=1)[C:7]([O:9][CH3:10])=[O:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 27339863-Fluorophenylboronic acidHCID 18766370Methyl 4-(bromomethyl)-3-fluorobenzoate

Product 1

HCID 67973755HCID 67973755, compoundYield 66%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalyst
HCID 962WaterSolvent
HCID 80711,2-DimethoxyethaneSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

Methyl 4-(bromomethyl)-3-fluorobenzoate (0.285 g; 1.15 mmol) was suspended in a mixture of water (1 mL) and 1,2-dimethoxyethane (3 mL) and 3-fluorophenylboronic acid (0.183 g; 1.27 mmol), tetrakis(triphenylphosphine)palladium(0) (0.067 g; 0.0058 mmol) and sodium carbonate (0.246 g; 2.31 mmol) were successively added. The resulting suspension was heated at 130° C. in a microwave oven for 20 minutes. The reaction mixture was diluted with ethyl acetate, and washed with water. The organic layer was concentrated under reduced pressure and the residue was purified by flash chromatography on silica gel (eluent 1 to 12% of ethyl acetate in heptane) to give 0.199 g (66%) of methyl 3-fluoro-4-(3-fluorobenzyl)benzoate as an oily residue which was directly used in the next step.

Workup

  1. additionwere successively added
  2. washwashed with water
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customthe residue was purified by flash chromatography on silica gel (eluent 1 to 12% of ethyl acetate in heptane)

Sources & evidence

ORD record
ord-10c7698e4600432a940c9bfdb772fa9e
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09266832B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes