Hydrochloric Acid → 4-Bromo-2-(trifluoromethoxy)benzoic acid

HRID 1984882ノート

反応式

HRID 1984882 の反応式
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([O:10][C:11]([F:14])([F:13])[F:12])[CH:3]=1.S(N)(=O)(=O)[OH:16].O.O.P([O-])(O)(O)=O.[Na+].Cl([O-])=O.[Na+].C([O-])([O-])=O.[Na+].[Na+].Cl>O1CCOCC1.O>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]([OH:16])=[O:7])=[C:4]([O:10][C:11]([F:12])([F:13])[F:14])[CH:3]=1

参加物

9

反応物 6

HCID 313Hydrochloric AcidHCID 5987Sulfamic AcidHCID 10340Sodium CarbonateHCID 187000874-Bromo-2-(trifluoromethoxy)benzaldehydeHCID 23668197Sodium ChloriteHCID 23673460Sodium Phosphate, Monobasic, Dihydrate

生成物 1

HCID 166655724-Bromo-2-(trifluoromethoxy)benzoic acid収率 81%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 312751,4-Dioxane溶媒

反応条件

温度
4 °C

実験手順

A solution of 4-bromo-2-trifluoromethoxy-benzaldehyde (550 mg, 2.04 mmol) in 1,4-dioxane (27 mL) and H2O (9 mL) was cooled at 4° C. To the solution were added amidosulfuric acid (296 mg, 3.05 mmol) and sodium dihydrogen phosphate dihydrate (1.4 g, 8.98 mmol). The mixture was stirred at 4° C. for 15 min. To the reaction mixture was added a solution of sodium chlorite (238 mg, 2.63 mmol) in H2O (1.5 mL) and stirred at 4° C. for 15 min. To the reaction mixture was added Na2CO3 (304 mg, 2.41 mmol) and stirred at 4° C. for 15 min. The mixture was acidified with conc-HCl (pH=1), and the aqueous layer was extracted with CHCl3 (three times). The combined organic layer was dried over MgSO4, filtered, concentrated, and purified by flash chromatography (silica gel, 1% MeOH in CHCl3) to give 4-bromo-2-trifluoromethoxy-benzoic acid (471 mg, 81%) as a white solid.

後処理

  1. stirringstirred at 4° C. for 15 min
  2. stirringstirred at 4° C. for 15 min
  3. extractionthe aqueous layer was extracted with CHCl3 (three times)
  4. dry with materialThe combined organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash chromatography (silica gel, 1% MeOH in CHCl3)

出典と根拠

ORDレコード
ord-229d4df18a5f4f82bc7e229e9dc16474
出典データセット
uspto-grants-2009_06
特許番号
US07544690B2

反応ノート

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