Carbon tetrabromide → HCID 59864791, compound

HRID 2423284Notes

Reaction equation

HRID 2423284 reaction equation
[CH3:1][C:2]1[C:9]([CH3:10])=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:13](Br)(Br)([Br:15])[Br:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:14][C:13]([Br:15])=[CH:4][C:3]1[CH:6]=[CH:7][C:8]([O:11][CH3:12])=[C:9]([CH3:10])[C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 5960582,3-Dimethyl-p-anisaldehyde

Product 1

HCID 59864791HCID 59864791, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Under an N2 atmosphere, 2,3-dimethylanisaldehyde (3.0 g, 18.3 mmol) was dissolved in dichloromethane (100 mL) and cooled to 0° C. Carbon tetrabromide (9.10 g, 27.4 mmol) was added followed by a dropwise addition of triphenylphosphine (14.4 g, 54.9 mmol) in dichloromethane (100 mL). The reaction was allowed to stir at 1.5 h at 0° C. The reaction was concentrated in vacuo, and the resulting residue was suspended in a mixture of hexanes and chloroform (4:1). The solid was removed by filtration and discarded. The filtrate was concentrated in vacuo and flash column chromatographed on silica gel eluting with 0% to 40% ethyl acetate in hexanes to yield the desired product. 1H NMR (400 MHz) (CDCl3) δ 7.44 (s, 1H); 7.19 (d, J=8.0 Hz, 1H): 6.72 (d, J=8.0 Hz, 1H), 3.82 (s, 3H); 2.17 (s, 3H); 2.16 (s, 3H).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. additionthe resulting residue was suspended in a mixture of hexanes and chloroform (4:1)
  3. customThe solid was removed by filtration
  4. concentrationThe filtrate was concentrated in vacuo and flash column
  5. customchromatographed on silica gel eluting with 0% to 40% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-0a7ddaaf9c7e4720817444bb5a477429
Source dataset
uspto-grants-2011_06
Patent number
US07960567B2

Reaction notes

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