Carbon tetrabromide → HCID 67502077, compound

HRID 1919307Notes

Reaction equation

HRID 1919307 reaction equation
O[CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[C:12]([C:18]([F:21])([F:20])[F:19])[CH:11]=2)[CH2:6][CH2:5]1.C(=O)([O-])[O-].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:48]>ClCCl>[Br:48][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[C:12]([C:18]([F:21])([F:20])[F:19])[CH:11]=2)[CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 11205Carbon tetrabromideHCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 43592139HCID 43592139, compound

Product 1

HCID 67502077HCID 67502077, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of alcohol 30a (35 mg, 0.12 mmol) in dichloromethane (4 mL) at 0° C. were added potassium carbonate (71 mg, 0.51 mmol), triphenylphosphine (88 mg, 0.34 mmol), and carbon tetrabromide (112 mg, 0.35 mmol). The solution was allowed to return at room temperature and was stirred for 90 min. The resulting solution was diluted with dichloromethane (25 mL), washed with a 10% sodium bicarbonate solution and filtered over a cotton plug. Purification of the resulting crude product by flash chromatography using ethyl acetate/hexane (7:3) as an eluant gave the desired compound 31a (22 mg, 60%). 1H NMR (400 MHz, Acetone-d6) δ: 2.71 (t, 4H, J=5.12 Hz), 2.82 (m, 2H), 3.56 (m, 6H), 7.27 (dd, 1H, J1=6.23 Hz, J2=2.61 Hz), 7.35 (d, 1H, J=2.53 Hz), 7.78 (d, 1H, J=8.84 Hz).

Workup

  1. customto return at room temperature
  2. washwashed with a 10% sodium bicarbonate solution
  3. filtrationfiltered over a cotton plug
  4. customPurification of the resulting crude product by flash chromatography

Sources & evidence

ORD record
ord-9437025f07e441b599f05ac977be4bc9
Source dataset
uspto-grants-2012_05
Patent number
US08168627B2

Reaction notes

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