Pentane → HCID 58993526, compound

HRID 391432Notes

Reaction equation

HRID 391432 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)[CH:5]=[C:6]([CH:8](O)[CH3:9])[CH:7]=1.C(Br)(Br)(Br)[Br:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCCCC>O1CCCC1>[Br:20][CH:8]([C:6]1[CH:5]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)[CH:3]=[C:2]([Cl:1])[CH:7]=1)[CH3:9]

Participants

6

Reactant 4

HCID 8003PentaneHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 58993635HCID 58993635, compound

Product 1

HCID 58993526HCID 58993526, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (±)-3′-chloro-5′-(1-hydroxyethyl)biphenyl-4-carbonitrile (171 mg, 0.664 mmol) and carbon tetrabromide (264 mg, 0.796 mmol) in tetrahydrofuran (2 mL) at 0° C. was added triphenylphosphine (209 mg, 0.796 mmol). The resulting solution was stirred at room temperature for 45 min. The reaction was diluted with ca. 2 volumes of pentane and filtered to remove the undissolved solids which were discarded. The organics were concentrated and purified by column chromatography (3%→8% ethyl acetate/hexanes) to give 201 mg (94%) as a colorless oil. 1H-NMR (CDCl3, 500 MHz) δ 7.74 (d, J=8.2 Hz, 2H), 7.66 (d, J=8.2 Hz, 2H), 7.50 (s, 1H), 7.47 (s, 2H), 5.18 (q, J=6.7 Hz, 1H), 2.06 (d, J=7.0 Hz, 3H); 13C NMR (126 MHz, CDCl3) δ ppm 146.1, 143.8, 141.5, 135.4, 132.8, 127.9, 127.3, 127.1, 124.2, 118.6, 112.1, 47.4, 26.8.

Workup

  1. additionThe reaction was diluted
  2. filtrationfiltered
  3. customto remove the undissolved solids which
  4. concentrationThe organics were concentrated
  5. custompurified by column chromatography (3%→8% ethyl acetate/hexanes)
  6. customto give 201 mg (94%) as a colorless oil

Sources & evidence

ORD record
ord-797ad753c99948578a38dfe19edb69ea
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Reaction notes

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