海萝胶 → 3-Bromo-5-(hydroxymethyl)benzoic acid

HRID 14101

反应方程式

HRID 14101 反应方程式
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([O:13]C)=[O:12])[CH:10]=1)[C:5](O)=[O:6].[BH4-].[Li+].C(O)C.Cl>O1CCCC1>[Br:1][C:2]1[CH:10]=[C:9]([CH:8]=[C:4]([CH2:5][OH:6])[CH:3]=1)[C:11]([OH:13])=[O:12]

参与物

6

反应物 4

HCID 313海萝胶HCID 702乙醇HCID 4148881硼氢化锂HCID 225936413-溴-5-羧基苯甲酸甲酯

产物 1

HCID 81671273-Bromo-5-(hydroxymethyl)benzoic acid

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂

实验过程

To an ice-cold solution of 3-bromo-5-(methoxycarbonyl)benzoic acid prepared by the method in Preparation 2 (10.3 g, 40 mmol) in anhydrous tetrahydrofuran (100 mL) is added lithium borohydride (12 g, 550 mmol) portion-wise. The reaction is stirred 4 h at this temperature. Absolute ethanol (20 mL) is added dropwise, and the reaction is stirred 1.5 h. The reaction is slowly poured on ice, and 10% hydrochloric acid (aq) is added until gas evolution ceased. The aqueous layer is extracted with chloroform, and the organic layer is washed with brine, dried (magnesium sulfate), filtered, and concentrated under reduced pressure to give the title compound. ESI MS m/z 229, 231 [M−H]−.

后处理

  1. stirringthe reaction is stirred 1.5 h
  2. additionis added until gas evolution
  3. extractionThe aqueous layer is extracted with chloroform
  4. washthe organic layer is washed with brine
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

来源与证据

ORD记录
ord-479f562303ec43e8b64ace9bb92a85a5
来源数据集
uspto-grants-2010_06
专利号
US07727997B2

关联笔记

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