Carbon tetrabromide → HCID 67324761, compound

HRID 1397373Notes

Reaction equation

HRID 1397373 reaction equation
[C:1]1([C:7]2[S:8][C:9]([CH2:12]O)=[CH:10][N: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:34]>C(Cl)Cl>[Br:34][CH2:12][C:9]1[S:8][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:11][CH:10]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 16495207(2-phenylthiazol-5-yl)Methanol

Product 1

HCID 67324761HCID 67324761, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(2-phenylthiazol-5-yl)methanol (390 mg, 2.03 mmol) was dissolved in dry CH2Cl2 (10 mL) and cooled to 0° C. Triphenyl phosphine (800 mg, 3.05 mmol) was then added, followed by carbon tetrabromide (1.35 g, 4.07 mmol). The reaction mixture was allowed to warm up to room temperature and stirred for 1 h. The reaction mixture was then concentrated under reduced pressure and the crude product was purified by column chromatography (silica 60-120 mesh, eluant 5% EtOAc in petroleum ether) to get 5-(bromomethyl)-2-phenylthiazole (250 mg, yield 48%) as light yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.95-7.92 (m, 2H), 7.80 (s, 1H), 7.46-7.45 (m, 3H), 4.77 (s, 2H). MS (ESI) m/z: Calculated for C10H8BrNS: 254.95. found: 256.0 (M+H)+.

Workup

  1. temperatureto warm up to room temperature
  2. concentrationThe reaction mixture was then concentrated under reduced pressure
  3. customthe crude product was purified by column chromatography (silica 60-120 mesh, eluant 5% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-c0f6219576c74350a34d252e6370beec
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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