Triphenylphosphine → 5-Bromo-2-methoxy-3-methylbenzyl bromide

HRID 391446Notes

Reaction equation

HRID 391446 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:12])[C:5]([O:10][CH3:11])=[C:6]([CH2:8]O)[CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:32]N1C(=O)CCC1=O>O1CCCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH3:12])[C:5]([O:10][CH3:11])=[C:6]([CH2:8][Br:32])[CH:7]=1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 58993702(5-Bromo-2-methoxy-3-methylphenyl)methanol

Product 1

HCID 589936415-Bromo-2-methoxy-3-methylbenzyl bromide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

(5-Bromo-2-methoxy-3-methylphenyl)methanol (2.0 g, 8.7 mmol) and triphenylphosphine (4.5 g, 17.4 mmol) were combined in tetrahydrofuran (30 mL) and cooled to 0° C. N-Bromosuccinimide (3.2 g, 17.4 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 (hexanes) gave 1.87 g (73%) as a white powder. 1H-NMR (CDCl3, 300 MHz) δ 7.32-7.33 (m, 1H), 7.23-7.24 (m, 1H), 4.46 (s, 2H), 3.82 (s, 3H), 2.25 (s, 3H).

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 (hexanes) gave 1.87 g (73%) as a white powder

Sources & evidence

ORD record
ord-95f3afa6728e4c50a9d9f5bc1ca5092e
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Reaction notes

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