Dichloromethane → HCID 135874460, compound

HRID 2102837Notes

Reaction equation

HRID 2102837 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([Cl:9])=[C:4]([C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2[O:17]C)[N:3]=1.C(Cl)Cl.B(Br)(Br)Br>O>[Cl:16][C:14]1[CH:13]=[CH:12][C:11]([OH:17])=[C:10]([C:4]2[C:5]([Cl:9])=[C:6]([Cl:8])[N:7]=[C:2]([Cl:1])[N:3]=2)[CH:15]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 24854608HCID 24854608, compound

Product 1

HCID 135874460HCID 135874460, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 250 mL 2-neck flask fitted with a rubber septum, temperature probe, and addition funnel was charged with 2,4,5-trichloro-6-(5-chloro-2-methoxy-phenyl)-pyrimidine (5.97 g, 18.54 mmol) and CH2Cl2 (90 mL) and kept under a N2 atmosphere. BBr3 (1 M in CH2Cl2; 37.1 mL, 37.1 mmol, 2 equiv.) was added slowly via addition funnel so that the temperature never exceeded 25° C. After 1 h, water (90 mL) was added and the mixture was stirred for approximately 30 min. The organic layer was washed with satd. aq. NaHCO3, dried, and concentrated to give a yellow powder (5.6 g, 98%). MS (ESI+): mass calcd. for C10H5Cl4N2O, 308.9; m/z found, 308.9 [M+H]+. 1H NMR (CDCl3): 9.76 (s, 1H), 8.00 (d, J=2.6 Hz, 1H), 7.39 (dd, J=8.9, 2.6 Hz, 1H), 7.03 (d, J=8.9 Hz, 1H).

Workup

  1. customA 250 mL 2-neck flask fitted with a rubber septum, temperature probe, and addition funnel
  2. washThe organic layer was washed with satd
  3. dry with materialaq. NaHCO3, dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8eb1f30ef18f46a9abc6bbce5aa6189c
Source dataset
uspto-grants-2009_08
Patent number
US07576092B2

Reaction notes

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