Water → 4-(Bromomethyl)benzaldehyde

HRID 2166836Notes

Reaction equation

HRID 2166836 reaction equation
[Br:1][CH2:2][C:3]1[CH:4]=[C:5](C(Cl)=O)[C:6]([CH3:9])=[CH:7][CH:8]=1.[H-].C([O:18][Al](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+].O>O1CCCC1>[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[O:18])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 16710494Lithium tri-tert-butoxyaluminohydrideHCID 86738932HCID 86738932, compound

Product 1

HCID 112064214-(Bromomethyl)benzaldehydeYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of the 4-bromomethyltoluoyl chloride (3.48 g. 15 mmol) in dry tetrahydrofuran (15 ml) was added dropwise to a solution of lithium tri-t-butoxyaluminium hydride (3.81 g, 15 mmol) in dry tetrahydrofuran (50 ml) at -70° C., stirred for 2 h, allowed to warm to room temperature and stirred for a further 1 h. The reaction was poured into water, filtered, extracted with ethyl acetate, dried (magnesium sulphate), and evaporated in vacuo to yield 4-bromomethylbenzaldehyde (1.31 g, 44%).

Workup

  1. stirringstirred for a further 1 h
  2. filtrationfiltered
  3. extractionextracted with ethyl acetate
  4. dry with materialdried (magnesium sulphate)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-cf26828819614fd2b0549d7a956348f2
Source dataset
uspto-grants-1983_06
Patent number
US04389410

Reaction notes

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