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

HRID 643279Notes

Reaction equation

HRID 643279 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Br:15])[CH:11]=2)[CH:6]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[Br:15][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[CH:6]=[C:5]([CH2:3][OH:2])[CH:14]=[CH:13]2

Participants

4

Reactant 2

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

Product 1

HCID 13473070(6-Bromonaphthalen-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl-6-bromo-2-naphtoate (25 g, 94.3 mmol) was reduced with lithiumaluminiumhydride (5.36 g, 141.4 mmol) in tetrahydrofuran (200 ml). The crystalline product was recrystallized from ethanol (96%). Yield 15.84 g (70.8%).

Workup

  1. customThe crystalline product was recrystallized from ethanol (96%)

Sources & evidence

ORD record
ord-da364bd7ed204dd4bf273626c15fda0b
Source dataset
uspto-grants-2010_04
Patent number
US07700596B2

Reaction notes

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