Carbon tetrabromide → 4-Bromomethyl-2-phenylthiophene

HRID 915694Notes

Reaction equation

HRID 915694 reaction equation
[C:1]1([C:7]2[S:11][CH:10]=[C:9]([CH2:12]O)[CH:8]=2)[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]>O1CCCC1.CC#N>[Br:34][CH2:12][C:9]1[CH:8]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[S:11][CH:10]=1

Participants

6

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 12941346(5-Phenylthiophen-3-yl)methanol

Product 1

HCID 198410854-Bromomethyl-2-phenylthiopheneYield 98.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Prepare a solution of (5-phenylthiophene-3-yl)methanol (394 mg, 2.07 mmol) in tetrahydrofuran (30 mL). Cool to 0° C. under nitrogen. Add PPh3 (723 mg, 2.75 mmol). Add dropwise a solution of carbon tetrabromide (912 mg, 2.75 mmol) in CH3CN (15 mL). Stir the reaction at 0° C. for 2 hours, then warm to room temperature overnight. Concentrate the mixture and flash-chromatograph on silica gel eluting with 7:3 ethyl acetate/hexane to afford 515 mg of 4-bromomethyl-2-phenylthiophene as a white solid. MS: m/e=254 [MH+].

Workup

  1. customthe reaction at 0° C. for 2 hours
  2. temperaturewarm to room temperature overnight
  3. concentrationConcentrate the mixture and flash-chromatograph on silica gel eluting with 7:3 ethyl acetate/hexane

Sources & evidence

ORD record
ord-30fece53bc054ed6ad6dd2496e95cc54
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

Loading…