5-Bromothiophene-2-carbaldehyde → HCID 12539266, compound

HRID 1895808Notes

Reaction equation

HRID 1895808 reaction equation
Br[C:2]1[S:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=1.[CH2:9](C([Sn])=C(CCCC)CCCC)[CH2:10]CC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:9]([C:2]1[S:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=1)=[CH2:10]

Participants

5

Reactant 2

HCID 784285-Bromothiophene-2-carbaldehydeHCID 53438229Tri(butyl)vinyltin

Product 1

HCID 12539266HCID 12539266, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A solution of 5-bromo-thiophene-2-carbaldehyde (1 g, 5.23 mmol) in anhydrous toluene (20 mL), at room temperature and under an atmosphere of nitrogen, was treated with tetrakis(triphenylphosphine)palladium(0) (121 mg, 0.1 mmol) and tributylvinyltin (2.3 mL, 7.85 mmol). The reaction was heated to reflux for 1 hour, after which it was cooled and the volatiles removed in vacuo. The product was purified by silica gel chromatography using iso-hexanes/ethyl acetate 10:1 to afford the title compound (623 mg, 85%) as a yellow oil. 1H NMR (300 MHz, CDCl3) δ 5.42 (d, J=10.9 Hz, 1H), 5.84 (d, J=17.4 Hz, 1H), 6.84 (dd, J=17.4, 10.9 Hz, 1H), 7.09 (d, J=4.0 Hz, 1H), 7.66 (d, J=3.8 Hz, 1H), 9.88 (s, 1H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 1 hour
  3. temperatureafter which it was cooled
  4. customthe volatiles removed in vacuo
  5. customThe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-ac09e95c9ec94056860e8963afb9104e
Source dataset
uspto-grants-2013_08
Patent number
US08513184B2

Reaction notes

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