Carbon tetrabromide → 954124-41-5

HRID 391428Notes

Reaction equation

HRID 391428 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9](O)[CH3:10])[CH:5]=[C:6]([F:8])[CH:7]=1.C(Br)(Br)(Br)[Br:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.CCCCC>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([CH:9]([Br:13])[CH3:10])[CH:3]=1

Participants

6

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 222402011-(3-broMo-5-fluorophenyl)ethanol

Product 1

HCID 58993668954124-41-5

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (±)-1-(3-bromo-5-fluorophenyl)ethanol (1.0 g, 4.6 mmol) and carbon tetrabromide (1.82 g, 5.48 mmol) in tetrahydrofuran (5 mL) at 0° C. was added triphenylphosphine (1.44 g, 5.48 mmol). The resulting solution was stirred at room temperature for 45 min. The reaction was diluted with several volumes of pentane, and filtered to remove the undissolved solids which were discarded. The organics were concentrated and purified by column chromatography (1% ethyl acetate/hexanes) to give 1.26 g (98%) as a colorless oil. 1H-NMR (CDCl3, 500 MHz) δ 7.35 (s, 1H), 7.17 (m, 1H), 7.09 (m, 1H), 5.06 (q, J=7.0 Hz, 1H), 2.00 (d, J=7.0 Hz, 3H); 13C NMR (126 MHz, CDCl3) δ ppm 163.6, 161.6, 147.2 (m), 126.0 (m), 122.8, 122.7, 119.2, 119.0, 113.3, 113.1, 46.5, 26.7.

Workup

  1. filtrationfiltered
  2. customto remove the undissolved solids which
  3. concentrationThe organics were concentrated
  4. custompurified by column chromatography (1% ethyl acetate/hexanes)
  5. customto give 1.26 g (98%) as a colorless oil

Sources & evidence

ORD record
ord-826719df704b4db38ef3a8d109aa5460
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Reaction notes

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