4-Cyanophenylboronic acid → Tert-butyl 4'-cyano-2-methyl-1,1'-biphenyl-4-carboxylate

HRID 392985Notes

Reaction equation

HRID 392985 reaction equation
Br[C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[CH:4][C:3]=1[CH3:15].[C:16]([C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1)#[N:17].BrCC1C=C(OC)C=CC=1C1C=CC(Cl)=CC=1>>[C:16]([C:18]1[CH:23]=[CH:22][C:21]([C:2]2[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[CH:4][C:3]=2[CH3:15])=[CH:20][CH:19]=1)#[N:17]

Participants

4

Reactant 3

HCID 27343264-Cyanophenylboronic acidHCID 11845988Tert-butyl 4-bromo-3-methylbenzoateHCID 219433382-(Bromomethyl)-4'-chloro-4-methoxy-1,1'-biphenyl

Product 1

HCID 22660788Tert-butyl 4'-cyano-2-methyl-1,1'-biphenyl-4-carboxylateYield 84%

Procedure

(Step 1) A solution of tert butyl 4-bromo-3-methylbenzoate (3.3 g, 12.2 mmol) was reacted with 4-cyanophenylboronic acid (2.15 g, 14.6 mmol) according to the procedure described for compound 14. The crude product was purified by column chromatography (silica gel, 3:2 hexanes/methylene dichloride) to afford tert-butyl 4′-cyano-2-methyl-1,1′-biphenyl-4-carboxylate as a white solid (3.0 g, 84% yield). ESI-MS m/e 294.1 (M+1).

Workup

  1. customThe crude product was purified by column chromatography (silica gel, 3:2 hexanes/methylene dichloride)

Sources & evidence

ORD record
ord-40c3058de5894d388df8dc30e959c41b
Source dataset
uspto-grants-2004_10
Patent number
US06803374B2

Reaction notes

Loading…