Water → 2,4-Dimethoxy-5-thien-2-ylbenzaldehyde

HRID 1270206Notes

Reaction equation

HRID 1270206 reaction equation
Br[C:2]1[C:3]([O:12][CH3:13])=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].[S:14]1[CH:18]=[CH:17][CH:16]=[C:15]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].O>COCCOC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:11][O:10][C:5]1[CH:4]=[C:3]([O:12][CH3:13])[C:2]([C:15]2[S:14][CH:18]=[CH:17][CH:16]=2)=[CH:9][C:6]=1[CH:7]=[O:8]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 6683465-Bromo-2,4-dimethoxybenzaldehydeHCID 27339602-Thiopheneboronic acid

Product 1

HCID 161161832,4-Dimethoxy-5-thien-2-ylbenzaldehydeYield 91%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Ex-1A: A solution of 5-bromo-2,4-dimethoxy-benzaldehyde (10.0 g, 40.80 mmol) and thiophene-2-boronic acid (7.8 g, 60.96 mmol) in ethylene glycol dimethyl ether (250 mL) was stirred at room temperature under nitrogen for 15 min. Tetrakis(triphenylphosphine)-palladium(0) (4.85 g, 4.19 mmol) and a sodium carbonate solution (2 M, 70 mL) were then added, and the resulting mixture was refluxed under nitrogen overnight. Upon codling to room temperature the reaction was poured into water (250 mL) and extracted with dichloromethane (2×250 mL). The organic phase was dried over sodium sulfate, filtered, and the solvent was removed under reduced pressure. Silica gel chromatography (hexane/ethyl acetate, 3:1) gave 9.2 g (91%) of the desired 2,4-dimethoxy-5-thiophen-2-yl-benzaldehyde product as a pale yellow solid, m.p. 125–126° C. 1H-NMR (300 MHz, CDCl3) δ 10.34 (s, 1H), 8.12 (s, 1H), 7.44 (dd, 1H, J=3.5 and 1.5 Hz), 7.31 (dd, 1H, J=5.2 and 1.5 Hz), 7.07 (dd, 1H, J=5.2 and 3.5 Hz), 6.51 (s, 1H), 4.02 (s, 3H), 3.99 (s, 3H)

Workup

  1. temperaturethe resulting mixture was refluxed under nitrogen overnight
  2. customUpon codling to room temperature
  3. extractionextracted with dichloromethane (2×250 mL)
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a1e7e7aef73644b4a367dcf97ff3aa53
Source dataset
uspto-grants-2007_04
Patent number
US07202247B2

Reaction notes

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