Hydrochloric Acid → 3-Bromo-5-(hydroxymethyl)benzoic acid

HRID 348893

反応式

HRID 348893 の反応式
[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].O=S1(=O)CC(N)C2C=CC=CC=2N1.[BH4-].[Li+].Cl>O1CCCC1.C(O)C>[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]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 225936413-Bromo-5-(methoxycarbonyl)benzoic acidHCID 588027552,2-Dioxo-1,2,3,4-tetrahydro-2lambda6-benzo[c][1,2]thiazin-4-ylamine

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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]−.

後処理

  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

出典と根拠

ORDレコード
ord-91d8f3927dd544c3b366b2775d57cab4
出典データセット
uspto-grants-2007_02
特許番号
US07176242B2

関連ノート

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