Triphenylphosphine → HCID 58993580, compound

HRID 391440Notes

Reaction equation

HRID 391440 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:15]O)[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:36]N1C(=O)CCC1=O>O1CCCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[CH:5]=[C:4]([CH2:15][Br:36])[CH:3]=1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 58993663HCID 58993663, compound

Product 1

HCID 58993580HCID 58993580, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

(5-Bromo-4′-fluorobiphenyl-3-yl)methanol (0.42 g, 1.5 mmol) and triphenylphosphine (0.78 g, 2.98 mmol) were combined in tetrahydrofuran (8 mL) and cooled to 0° C. N-Bromosuccinimide (0.59 g, 3.1 mmol) was introduced in portions and the reaction allowed to warm to room temperature. After 16 h, the reaction mixture was diluted with ethyl acetate, washed with concentrated sodium bicarbonate (2×), then brine (2×), dried over sodium sulfate, and concentrated. Column chromatography on silica gel (5% ethyl acetate/hexanes) gave 0.4 g (78%) as a white powder. 1H-NMR (CDCl3, 500 MHz) 7.60 (m, 1H), 7.50-7.54 (m, 3H), 7.47 (m, 1H), 7.12-7.15 (m, 2H), 4.47 (s, 2H).

Workup

  1. temperatureto warm to room temperature
  2. washwashed with concentrated sodium bicarbonate (2×)
  3. dry with materialbrine (2×), dried over sodium sulfate
  4. concentrationconcentrated
  5. customColumn chromatography on silica gel (5% ethyl acetate/hexanes) gave 0.4 g (78%) as a white powder

Sources & evidence

ORD record
ord-d0a09f4154524a51ad0ce7659eea07a9
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Reaction notes

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