Carbon tetrabromide → HCID 69129919, compound

HRID 915685Notes

Reaction equation

HRID 915685 reaction equation
[C:1]1([C:7]2[S:11][CH:10]=[N:9][C:8]=2[CH2:12]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Br)(Br)(Br)[Br:34]>CC#N>[Br:34][CH2:12][C:8]1[N:9]=[CH:10][S:11][C:7]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 59455496(5-Phenylthiazol-4-yl)methanol

Product 1

HCID 69129919HCID 69129919, compoundYield 21.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Prepare a cold (0° C.) solution of (5-phenyl-thiazol-4-yl)-methanol (1.4 g, 7.3 mmol) in CH3CN (50 mL). Add PPh3 (2.6 g, 9.7 mmol) and CBr4 (3.2 g, 9.7 mmol). Stir the reaction at 0° C. for 3 hours, allow to warm to room temperature and then concentrate in vacuo to an oil. Chromatograph (silica gel, 4:1 Hex/ethyl acetate) to afford the title compound (400 mg). 1H NMR (CDCl3) δ 8.80 (s, 1H), 7.40-7.60 (m, 5H), 4.65 (s, 2H).

Workup

  1. customthe reaction at 0° C. for 3 hours
  2. concentrationconcentrate in vacuo to an oil

Sources & evidence

ORD record
ord-c61eb2806a3f4f66ba91c8779bcf97ca
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

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