1-Bromo-3-chloropropane → 2-Chloro-4-(3-chloro-propoxy)-benzaldehyde

HRID 2420971Notes

Reaction equation

HRID 2420971 reaction equation
Br[CH2:2][CH2:3][CH2:4][Cl:5].[Cl:6][C:7]1[CH:14]=[C:13]([OH:15])[CH:12]=[CH:11][C:8]=1[CH:9]=[O:10].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[Cl:6][C:7]1[CH:14]=[C:13]([O:15][CH2:2][CH2:3][CH2:4][Cl:5])[CH:12]=[CH:11][C:8]=1[CH:9]=[O:10]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 1853632-Chloro-4-hydroxybenzaldehyde

Product 1

HCID 574347552-Chloro-4-(3-chloro-propoxy)-benzaldehydeYield 84.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

1-Bromo-3-chloropropane (2.55 g, 16.2 mmol, 1.0 equiv) was added to a solution of 2-chloro-4-hydroxybenzaldehyde (2.54 g, 16.2 mmol) and K2CO3 (4.48 g, 32.4 mmol) in acetonitrile (41 mL). The mixture was heated at 65° C. for 18 h, then cooled to room temperature (rt) and filtered through diatomaceous earth. The filtrate was concentrated to yield the crude product, which was purified by column chromatography (silica gel, 5% EtOAc in hexanes) to afford 3.19 g of a colorless oil (66%). 1H NMR (400 MHz, CD3OD): 10.3 (s, 1H), 7.87 (d, J=8.0, 1H), 7.10 (d, J=4.0, 1H), 7.03 (dd, J=8.0, 4.0, 1H), 4.23 (t, J=8.0, 2H), 3.76 (t, J=8.0, 2H), 2.31-2.22 (m, 2H).

Workup

  1. temperaturecooled to room temperature (rt)
  2. filtrationfiltered through diatomaceous earth
  3. concentrationThe filtrate was concentrated
  4. customto yield the crude product, which
  5. customwas purified by column chromatography (silica gel, 5% EtOAc in hexanes)

Sources & evidence

ORD record
ord-312364090d3644958e9d920eb3b0a2ba
Source dataset
uspto-grants-2011_06
Patent number
US07956066B2

Reaction notes

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