Sodium Thiosulfate Pentahydrate → Tert-butyl 3-bromo-5-formylbenzoate

HRID 1257525ノート

反応式

HRID 1257525 の反応式
[Br-].[K+].CC1(C)N([O])C(C)(C)CCC1.[Br:14][C:15]1[CH:16]=[C:17]([CH:25]=[C:26]([CH2:28][OH:29])[CH:27]=1)[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].Cl[O-].[Na+].O.O.O.O.O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(=O)(O)[O-].[Na+].O.ClCCl>[Br:14][C:15]1[CH:16]=[C:17]([CH:25]=[C:26]([CH:28]=[O:29])[CH:27]=1)[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]

参加物

9

反応物 5

HCID 61475Sodium Thiosulfate PentahydrateHCID 253877Potassium BromideHCID 2724126TempoHCID 23665760Sodium HypochloriteHCID 58096191Tert-butyl 3-bromo-5-(hydroxymethyl)benzoate

生成物 1

HCID 58095966Tert-butyl 3-bromo-5-formylbenzoate

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 6344Dichloromethane溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a suspension of potassium bromide (249.3 g, 2.095 mol), 2,2,6,6-tetramethylpiperidine 1-oxyl (3.27 g, 20.93 mmol) in saturated aqueous sodium bicarbonate (960 mL) and water (240 mL) were added tert-butyl 3-bromo-5-(hydroxymethyl)benzoate (119.7 g, 417 mmol) and dichloromethane (1200 mL). The mixture was cooled to <5° C. and sodium hypochlorite (850 mL, 12.53 mol) was added dropwise in 4 portions until the reaction completed. A solution of sodium thiosulfate pentahydrate (72 g) in water (250 mL) was added and the reaction mixture was warmed to ambient temperature. The organic layer was separated and the aqueous layer was extracted with dichloromethane (2×). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated (119.0 g).

後処理

  1. temperatureThe mixture was cooled to <5° C.
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with dichloromethane (2×)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated (119.0 g)

出典と根拠

ORDレコード
ord-d48244ab4a1e49c7bf7736ebdd649576
出典データセット
uspto-grants-2013_06
特許番号
US08461185B2

反応ノート

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