Carbon tetrabromide → HCID 13593314, compound

HRID 2304567Notes

Reaction equation

HRID 2304567 reaction equation
[Cl:1][C:2]1[C:11]([CH2:12]O)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:33]C(Br)(Br)Br>>[Br:33][CH2:12][C:11]1[C:2]([Cl:1])=[N:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

4

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 930708(2-chloroquinolin-3-yl)methanol

Product 1

HCID 13593314HCID 13593314, compoundYield 66%

Procedure

A solution under argon of 2-chloro-3-quinolylmethanol (obtained according to 4.a, 15.5 g 80 mmol) and triphenylphosphine (32 g, 120 mmol) is treated with small portions of tetrabromomethane (40 g, 120 mmol) while keeping the temperature of the reaction medium below 30° C. After agitation under argon for 2 hours at ambient temperature, the reaction medium is concentrated under reduced pressure, and the residue is purified by column chromatography (SiO2, ethyl acetate/heptane: 1/1) in order to produce 13.5 g (66%) of a white solid, m.p. 125° C.

Workup

  1. customthe temperature of the reaction medium below 30° C
  2. concentrationthe reaction medium is concentrated under reduced pressure
  3. customthe residue is purified by column chromatography (SiO2, ethyl acetate/heptane: 1/1) in order

Sources & evidence

ORD record
ord-fc0e2a92d6324265b66413ab0b5eded3
Source dataset
uspto-grants-2002_08
Patent number
US06436951B1

Reaction notes

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