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

HRID 1427797Notes

Reaction equation

HRID 1427797 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) δ5.42 (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-7938ffccbf66468988c9d858b1db7ab6
Source dataset
uspto-grants-2015_01
Patent number
US08933015B2

Reaction notes

Loading…