2-Bromo-6-methoxycarbonylnaphthalene → (6-Bromonaphthalen-2-yl)methanol

HRID 541494Notes

Reaction equation

HRID 541494 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[CH:14]=[C:13]([C:18](OC)=[O:19])[CH:12]=[CH:11]2>C1COCC1>[Br:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[CH:14]=[C:13]([CH2:18][OH:19])[CH:12]=[CH:11]2

Participants

4

Reactant 2

HCID 8541342-Bromo-6-methoxycarbonylnaphthaleneHCID 21226445Aluminium lithium hydride

Product 1

HCID 13473070(6-Bromonaphthalen-2-yl)methanolYield 75.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a three-necked flask (5 L) cooled with an ice-bath was added lithium aluminum hydride (40 g, 1.05 mol), and anhydrous THF (500 mL) under nitrogen protection. To this suspension, Methyl 6-bromo-2-naphthoate (141 g, 0.534 mol) dissolved in anhydrous THF (1200 mL) was added dropwise slowly through a dropping funnel. Cooling bath was removed and the reaction mixture was kept under stirring for additional 2 hours. The reaction mixture was cooled with an ice-bath again, and to it was added methanol (150 mL) dropwise carefully until there was no gas release. The mixture was kept under stirring for half an hour and then was acidified with concentrated hydrochloric acid to a PH of about 4. The resulting solid was removed by filtering under reduced pressure and the filtrate was concentrated, and then poured into deionized water (2 L). The resulting precipitate was collected by suction filter, and washed with deionized water, followed by a little ethanol, and dried in vacuum to afford (6-bromonaphthalen-2-yl)methanol (95.4 g).

Workup

  1. temperatureTo a three-necked flask (5 L) cooled with an ice-bath
  2. additionwas added dropwise slowly through a dropping funnel
  3. temperatureCooling bath
  4. customwas removed
  5. temperatureThe reaction mixture was cooled with an ice-bath again
  6. additionto it was added methanol (150 mL) dropwise carefully until there
  7. stirringunder stirring for half an hour
  8. customThe resulting solid was removed
  9. filtrationby filtering under reduced pressure
  10. concentrationthe filtrate was concentrated
  11. additionpoured into deionized water (2 L)
  12. customThe resulting precipitate was collected by suction
  13. filtrationfilter
  14. washwashed with deionized water
  15. customdried in vacuum

Sources & evidence

ORD record
ord-244d5ca2497840e2aaff3b01be37a859
Source dataset
uspto-grants-2014_10
Patent number
US08872422B2

Reaction notes

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