Dichloromethane → HCID 67974355, compound

HRID 1777510Notes

Reaction equation

HRID 1777510 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].[F:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1.C(N(CC)C(C)C)(C)C.ClCCl>O.C(COC)OC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:13][C:14]1[CH:19]=[C:18]([CH:17]=[CH:16][CH:15]=1)[CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 517981Methyl 3-(bromomethyl)benzoateHCID 27339863-Fluorophenylboronic acid

Product 1

HCID 67974355HCID 67974355, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of methyl 3-(bromomethyl)benzoate (0.500 g; 2.18 mmol), 3-fluorophenylboronic acid (0.334 g; 2.40 mmol), N,N-diisopropylethylamine (0.752 mL; 4.37 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) chloride, complex with dichloromethane (0.178 g; 0.218 mmol) in water (1 mL) and dimethoxyethane (3 mL) was irradiated in a microwave oven at 130° C. for 15 minutes. The resulting mixture was partitioned between water and ethyl acetate and the phases were separated. The organic layer was washed with water and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel (eluent 2 to 40% ethyl acetate in heptane) to yield 0.265 g (50%) of methyl 3-(3-fluorobenzyl)benzoate.

Workup

  1. customwas irradiated in a microwave oven at 130° C. for 15 minutes
  2. customThe resulting mixture was partitioned between water and ethyl acetate
  3. customthe phases were separated
  4. washThe organic layer was washed with water
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by flash chromatography on silica gel (eluent 2 to 40% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-21c1e086a9f448e7ae37df90ce66acd2
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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