Water → 5-Bromobiphenyl-2-methanol

HRID 1499124Notes

Reaction equation

HRID 1499124 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:5]([C:14](OC)=[O:15])=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:14][OH:15])=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 54332024Methyl 5-bromo-[1,1'-biphenyl]-2-carboxylate

Product 1

HCID 1179418105-Bromobiphenyl-2-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 5-bromo-[1,1′-biphenyl]-2-carboxylate (2.2 g, 6.9 mmol) in THF (50 mL) was cooled to 0° C. LiAlH4 (380 mg, 10 mmol) was added slowly. The reaction mixture was stirred at RT for 2 h, after which water (1 mL) was added slowly to quench the reaction. The solid was removed by filtration and the filtrate was concentrated in vacuo to provide (5-bromo-[1,1′-biphenyl]-2-yl)methanol as a white solid that was used directly without further purification.

Workup

  1. customto quench
  2. customthe reaction
  3. customThe solid was removed by filtration
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-d9abe8955b0b490396eface5c0fdf6b8
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Reaction notes

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