Potassium Bromide → Methyl 3'-bromo-4'-methoxy-2-methylbiphenyl-4-carboxylate

HRID 2093138ノート

反応式

HRID 2093138 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][C:10]=2[CH3:19])=[CH:5][CH:4]=1.OOS([O-])=O.[K+].[K+].[Br-:27]>C(#N)C.O>[Br:27][C:8]1[CH:7]=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][C:10]=2[CH3:19])[CH:5]=[CH:4][C:3]=1[O:2][CH3:1]

参加物

6

反応物 3

HCID 253877Potassium BromideHCID 23707502Potassium hydroxy sulfiteHCID 67065985Methyl 4-(4-methoxyphenyl)-3-methylbenzoate

生成物 1

HCID 67066022Methyl 3'-bromo-4'-methoxy-2-methylbiphenyl-4-carboxylate

試薬・触媒・溶媒 2

HCID 962Water溶媒3 回HCID 6342Acetonitrile溶媒

実験手順

To a solution of methyl 4′-methoxy-2-methylbiphenyl-4-carboxylate (71.5 g, 0.279 mol) in acetonitrile (1.43 L) and water (572 mL) was added oxone (180.1 g, 0.293 mol). Then a solution of KBr (38.2 g, 0.321 mol) in water (143 mL) was slowly added over 30 minutes. The reaction was stirred for 2.5 hours, then water (715 mL) was added and the mixture was left standing for 1 hour. The solids were filtered and washed as follows: with a solution of MeCN/water (1:1, 350 mL, twice), water (700 mL, twice, then 350 mL) and dried to afford methyl 3′-bromo-4′-methoxy-2-methylbiphenyl-4-carboxylate. 1H NMR (CDCl3, 400 MHz) δ 7.94 (s, 1H), 7.89 (d, J=8.1 Hz, 1H), 7.53 (d, J=2.2 Hz, 1H), 7.3-7.2 (m, 2H), 6.97 (d, J=8.4 Hz, 1H), 3.96 (s, 3H), 3.94 (s, 3H), 2.32 (s, 3H).

後処理

  1. waitthe mixture was left
  2. waitstanding for 1 hour
  3. filtrationThe solids were filtered
  4. washwashed
  5. dry with materialwith a solution of MeCN/water (1:1, 350 mL, twice), water (700 mL, twice, then 350 mL) and dried

出典と根拠

ORDレコード
ord-eccd44ba9b164891b8f5db6d3f6e7cc9
出典データセット
uspto-grants-2013_05
特許番号
US08440702B2

反応ノート

読み込み中…