Carbon tetrabromide → HCID 66846510, compound

HRID 254160Notes

Reaction equation

HRID 254160 reaction equation
[C:1]1([C:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:8][CH2:9][C:10]2[N:15]=[C:14]([CH2:16]O)[CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:50]>C(Cl)Cl>[Br:50][CH2:16][C:14]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:9][O:8][C:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:15]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 4176130HCID 4176130, compound

Product 1

HCID 66846510HCID 66846510, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 6-(triphenylmethoxymethyl)pyridine-2-methanol (16.8 g, 44 mmol) in CH2Cl2 at 0° C. was treated with triphenylphosphine (17.3 g, 66 mmol) and carbon tetrabromide (17.5 g, 52.8 mmol), stirred at 0° C. for 2.5 h then concentrated in vacuo to approximately a quarter of the original volume. The resulting solution was filtered through a pad of silica, washed with hexane:EtOAc (1:1) and the filtrate concentrated in vacuo to give the title compound (16.8 g, 86%) as a cream solid; NMR δH (400 MHz, DMSO) 4.14 (2H, s), 4.61 (2H, s), 7.27-7.48 (16H, m), 7.68 (1H, d, J 7.5 Hz) and 7.90 (1H, t, J 7.5 Hz); Rf (Hexane:EtOAc (2:1))=0.84

Workup

  1. concentrationthen concentrated in vacuo to approximately a quarter of the original volume
  2. filtrationThe resulting solution was filtered through a pad of silica
  3. washwashed with hexane:EtOAc (1:1)
  4. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-aec5cdc4cccb4a01ada06e6469a66e35
Source dataset
uspto-grants-2011_01
Patent number
US07875600B2

Reaction notes

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