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

HRID 348893

Reaction equation

HRID 348893 reaction equation
[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]

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

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]−.

Workup

  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

Sources & evidence

ORD record
ord-91d8f3927dd544c3b366b2775d57cab4
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Linked notes

Loading…