Dimethylformamide → 4'-Bromo-[1,1'-biphenyl]-4-carbaldehyde

HRID 1182497Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[Li]CCCC.CN([CH:23]=[O:24])C>C1COCC1>[Br:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([CH:23]=[O:24])=[CH:3][CH:4]=2)=[CH:9][CH:10]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 4′,4-dibromobiphenyl (3.12 g, 10 mmol) in dry THF (50 mL) at −78° C. was added dropwise a solution of n-BuLi (1.6M in hexane, 10 mmol). After addition, the mixture was stirred for 30 minutes at −78° C. Anhydrous DMF (50 mL) was then added and the mixture was allowed to stir at room temperature for 2 hours. The solvent was removed under high vacuum and the residue was taken in water and extracted with dichloromethane (2×50 mL). The combined organic layer were dried (MgSO4) and concentrated. Purification by flash chromatography (ethyl acetate/hexane: 2/8) gave the title compound 152 55% yield. MS (ESI)=261 (MH+).

Workup

additionAfter addition
stirringto stir at room temperature for 2 hours
customThe solvent was removed under high vacuum
extractionextracted with dichloromethane (2×50 mL)
dry with materialThe combined organic layer were dried (MgSO4)
concentrationconcentrated
customPurification by flash chromatography (ethyl acetate/hexane: 2/8)

Sources & evidence

ORD record: ord-2b1a2eac20714682a1de1cee148d596e
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07288567B2

Reaction notes

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