Sodium Carbonate → 2-(4-Bromophenyl)naphthalene

HRID 909956Notes

Reaction equation

[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1B(O)O.[Br:14][C:15]1[CH:20]=[CH:19][C:18](I)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[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.C1(C)C=CC=CC=1>[Br:14][C:15]1[CH:20]=[CH:19][C:18]([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Under an argon gas atmosphere, 70.0 g (407 mmol) of 2-naphthalene boronic acid, 115.1 g (407 mmol 1) of 4-bromoiodobenzene, 9.40 g (8.14 mmol) of tetrakis(triphenylphosphine)palladium(0), 1.2 L of toluene and 600 ml of 2M sodium carbonate solution were mixed, and stirred for 20 hours at 90 degrees C. After the reaction in the mixture was over, toluene was distilled away therefrom, and the mixture was added with methanol, such that precipitated solid was separated by filtration. By recrystallizing the obtained solid by acetic ether and methanol and subsequently drying the solid, 77.2 g of 2(4-bromophenyl)naphthalene was obtained with an yield of 67%.

Workup

customAfter the reaction in the mixture
distillationwas distilled away
additionthe mixture was added with methanol, such that precipitated solid
customwas separated by filtration
customBy recrystallizing the obtained solid by acetic ether and methanol
customsubsequently drying the solid

Sources & evidence

ORD record: ord-bd8a5414a88942378b4e988ab0fd5f6b
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08021574B2

Reaction notes

Loading…