Carbon tetrabromide → HCID 67500546, compound

HRID 1919302Notes

Reaction equation

HRID 1919302 reaction equation
[CH3:1][C:2]1([CH3:25])[C:6]([CH3:10])([CH2:7][CH2:8]O)[C:5](=[O:11])[N:4]([C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[C:14]([C:20]([F:23])([F:22])[F:21])[CH:13]=2)[C:3]1=[O:24].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:46]>ClCCl>[CH3:1][C:2]1([CH3:25])[C:6]([CH3:10])([CH2:7][CH2:8][Br:46])[C:5](=[O:11])[N:4]([C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[C:14]([C:20]([F:23])([F:22])[F:21])[CH:13]=2)[C:3]1=[O:24]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 67501823HCID 67501823, compound

Product 1

HCID 67500546HCID 67500546, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of compound 20a (33 mg, 0.097 mmol) in anhydrous dichloromethane (2 mL) at 0° C. under argon were added triphenylphosphine (50 mg, 0.194 mmol) and carbontetrabromide (64 mg, 0.194 mmol). The solution was allowed to return to room temperature and stirred for 1 hr. The resulting solution was diluted with dichloromethane (25 mL) and filtered on a cotton plug. Purification of the resulting crude product by flash chromatography using a gradient of ethyl acetate/hexane (3:97 to 3:7) as an eluant gave the desired compound 21a (15 mg, 40% for 2 steps). 1H NMR (400 MHz, Acetone-d6) δ: 1.36 (s, 3H), 1.39 (s, 3H), 1.40 (s, 3H), 2.28 (m, 2H), 3.68 (m, 2H), 8.03 (dd, 1H, J1=6.57 Hz, J2=1.84 Hz), 8.14 (d, 1H, J=1.45 Hz), 8.24 (d, 1H, J=8.40 Hz).

Workup

  1. customto return to room temperature
  2. filtrationfiltered on a cotton plug
  3. customPurification of the resulting crude product by flash chromatography

Sources & evidence

ORD record
ord-72194fa333434a04aefac894f5a0ea8f
Source dataset
uspto-grants-2012_05
Patent number
US08168627B2

Reaction notes

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