反応 #309259

反応方程式

2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

methyl 4-bromobenzoate

Cs2CO3

→

desired product

収率 79.1%

Methyl 4′-hydroxy-3′,5′-dimethylbiphenyl-4-carboxylate

収率 79.1%

溶媒

DMF

EtOAc

反応条件

後処理

1. 1
   洗浄washed with H2O (2×50 mL)
2. 2
   乾燥dried over Na2SO4
3. 3
   その他Purification on a silica gel column

実験手順

A solution of 2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (525 mg, 2.12 mmol), methyl 4-bromobenzoate (460 mg, 2.14 mmol), PdCl2(dppf) (80 mg, 0.11 mmol) and Cs2CO3 (1.40 g, 4.31 mmol) in DMF (10 mL, 5% H2O) was heated at 80° C. for 1 h. The reaction mixture was diluted with EtOAc (50 mL), washed with H2O (2×50 mL), and dried over Na2SO4. Purification on a silica gel column gave the desired product as a pale yellow solid (430 mg). NMR (CDCl3): δ 8.08 (d, 2H), 7.62 (d, 2H), 7.29 (s, 2H), 4.75 (s, 1H), 3.95 (s, 3H), 2.35 (s, 6H).

出典