4-Hydroxybenzaldehyde → 4-(3-Bromopropoxy)benzaldehyde

HRID 1107717Notes

Reaction equation

HRID 1107717 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].[Br:12][CH2:13][CH2:14][CH2:15]Br.O>CN(C=O)C>[Br:12][CH2:13][CH2:14][CH2:15][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 80011,3-DibromopropaneHCID 24758Sodium hydride

Product 1

HCID 137157894-(3-Bromopropoxy)benzaldehydeYield 52.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 4-hydroxybenzaldehyde (3.7 g, 30 mmol) in DMF (10 ml) was added cautiously to a stirred solution of sodium hydride (60% in oil, 1.44 g) in DMF (80 ml). After 30 min., 1,3-dibromopropane (9.2 ml, 90 mmol) in DMF (10 ml) was added dropwise, the mixture stirred for 16 h, poured into water, extracted twice with ethyl acetate, and the combined extracts washed with water and saturated aqueous sodium chloride, dried over sodium sulphate and evaporated. The residue was purified by flash chromatography on silica, eluting with 25% diethyl ether in hexane, to afford 4-(3-bromopropyloxy)benzaldehyde (3.85 g). M+ 205; 360 MHz 1H n.m.r (CDCl3) 7.85 (2H, d, J 7.0 Hz), 7.01 (2H, d, J 7.0 Hz), 4.20 (2H, t, J 5.8 Hz), 3.62 (2H, t, J 6.4 Hz), 2.36 (2H, pentet, J 6.1 Hz).

Workup

  1. extractionextracted twice with ethyl acetate
  2. washthe combined extracts washed with water and saturated aqueous sodium chloride
  3. dry with materialdried over sodium sulphate
  4. customevaporated
  5. customThe residue was purified by flash chromatography on silica
  6. washeluting with 25% diethyl ether in hexane

Sources & evidence

ORD record
ord-9147e9e03b3043ffa032416cf7f88e0a
Source dataset
uspto-grants-2000_05
Patent number
US06063789

Reaction notes

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