Carbon tetrabromide → HCID 12147022, compound

HRID 1836324Notes

Reaction equation

HRID 1836324 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([S:27]([NH:30][C:31]1[C:32](=[O:42])[N:33]([CH2:38][CH2:39][CH2:40]O)[C:34]([CH3:37])=[CH:35][CH:36]=1)(=[O:29])=[O:28])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(Br)(Br)(Br)[Br:44]>CN(C=O)C>[CH2:20]([S:27]([NH:30][C:31]1[C:32](=[O:42])[N:33]([CH2:38][CH2:39][CH2:40][Br:44])[C:34]([CH3:37])=[CH:35][CH:36]=1)(=[O:29])=[O:28])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 12147021HCID 12147021, compound

Product 1

HCID 12147022HCID 12147022, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of triphenylphosphine (0.46 g, 1.75 mmol) in DMF (5 mL) was added to a mixture of 1-5 (0.49 g, 1.46 mmol) and carbon tetrabromide (0.68 g, 2.05 mmol) in DMF (5 mL) at 0° C. The resulting mixture was allowed to warm to room temperature and allowed to stir for 12 hours. The mixture was then concentrated under reduced pressure. The crude residue was purified by silica gel column chromatography using ethyl acetate and hexane (3:1 to 2:1 gradient) as eluants to afford the title compound 1-6 (0.38 g, 66% yield) as a yellow solid. MS (m/e): 399. TLC: Rf (0.35) (EA/Hex); 1H NMR (400 MHz, CDCl3): δ 2.23 (m, 2H), 2.4 (s, 3H), 3.5 (t, 2H), 4.2 (t, 2H), 4.3 (s, 2H), 6.0 (d, 1H), 7.2(d, 1H), 7.3(m, 5H).

Workup

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. customThe crude residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4b81294124094dd3a904690c292ccfbe
Source dataset
uspto-grants-2004_08
Patent number
US06777431B2

Reaction notes

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