Triphenylphosphine → 3-Bromo-5-(trifluoromethyl)benzyl bromide

HRID 391378Notes

Reaction equation

HRID 391378 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:12]O)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:33]N1C(=O)CCC1=O>O1CCCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([CH2:12][Br:33])[CH:3]=1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 29919767[3-Bromo-5-(trifluoromethyl)phenyl]methanol

Product 1

HCID 223242723-Bromo-5-(trifluoromethyl)benzyl bromide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

(3-Bromo-5-(trifluoromethyl)phenyl)methanol (1.6 g, 6.3 mmol) and triphenylphosphine (3.3 g, 12.6 mmol) were combined in tetrahydrofuran (30 mL) and cooled to 0° C. N-Bromosuccinimide (2.4 g, 13.2 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×), brine (2×), dried over sodium sulfate, and concentrated. Column chromatography on silica gel (100% hexanes) gave 1.53 g (76%) as a light brown oil. 1H-NMR (CDCl3, 500 MHz) δ 7.73 (s, 1H), 7.70 (s, 1H), 7.58 (s, 1H), 4.44 (s, 2H).

Workup

  1. temperatureto warm to room temperature
  2. washwashed with concentrated sodium bicarbonate (2×), brine (2×)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customColumn chromatography on silica gel (100% hexanes) gave 1.53 g (76%) as a light brown oil

Sources & evidence

ORD record
ord-9325a1dd70f6480f84c49dd132ffed85
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Reaction notes

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