Carbon tetrabromide → 2-(Bromomethyl)-5-chloropyridine

HRID 1044420Notes

Reaction equation

HRID 1044420 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8]O)=[N:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:30]>C(Cl)Cl>[Br:30][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 20537893(5-Chloropyridin-2-yl)methanol

Product 1

HCID 222705252-(Bromomethyl)-5-chloropyridineYield 16.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 0° C. solution of (5-chloropyridin-2-yl)methanol Part D (10 mg, 0.070 mmol) and triphenylphosphine (32.9 mg, 0.125 mmol) in DCM (0.170 mL) was added a solution of carbon tetrabromide (31.4 mg, 0.095 mmol) in DCM (0.084 mL) dropwise. The mixture was stirred at RT for 2.0 h at which point the solvent was removed in vacuo and the crude product was subjected to flash chromatography (silica gel/DCM-EtOAc 100:0 to 0:100 gradient) to afford 2-(bromomethyl)-5-chloropyridine 16E (2.4 mg, 16.8% yield) as a light brown oil. LC-MS, [M+H]+208. 1H NMR (400 MHz, CDCl3) δ 8.47 (1H, d, J=2.2 Hz), 7.61 (1H, dd, J=8.4, 2.2 Hz), 7.33 (1H, d, J=8.4 Hz), 4.46 (2H, s). HPLC-Method 8; 2.42 min.

Workup

  1. customwas removed in vacuo

Sources & evidence

ORD record
ord-ec352e008d7548808ee1ab5f72b6a2c5
Source dataset
uspto-grants-2013_10
Patent number
US08563583B2

Reaction notes

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