Carbon tetrabromide → HCID 57546042, compound

HRID 913906Notes

Reaction equation

HRID 913906 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]([CH2:20]O)[C:6]2[N:10]=[N:9][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:7]=2[CH:19]=1.C(Br)(Br)(Br)[Br:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Br:25][CH2:20][C:5]1[C:6]2[N:10]=[N:9][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:7]=2[CH:19]=[C:3]([C:2]([F:23])([F:22])[F:1])[CH:4]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 57546211HCID 57546211, compound

Product 1

HCID 57546042HCID 57546042, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (6-(trifluoromethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d][1,2,3]triazol-4-yl)methanol (165 mg, 0.475 mmol) and carbon tetrabromide (236 mg, 0.712 mmol) in tetrahydrofuran (2 mL) at 0° C. was added triphenylphosphine (187 mg, 0.712 mmol). The ice bath was removed and stirring continued at room temperature for 30 min. The reaction was diluted with several volumes of pentane and filtered to remove undissolved solids which were discarded. The organics were concentrated and purified by column chromatography (4→8% ethyl acetate/hexanes) to give 159 mg (82%) as a colorless oil. 1H-NMR (CDCl3, 500 MHz) δ 7.96 (s, 1H), 7.67 (s, 1H), 6.03 (s, 2H), 5.04 (s, 2H), 3.59 (m, 2H), 0.90 (m, 2H), −0.07 (s, 9H); 13C-NMR (CDCl3, 126 MHz) δ 145.9, 132.6, 131.6, 130.4 (q, J=33 Hz), 123.7 (q, J=273 Hz), 121.6 (q, J=2.9 Hz), 108.6 (q, J=4.8 Hz), 67.7, 25.9, 17.7, −1.5.

Workup

  1. customThe ice bath was removed
  2. additionThe reaction was diluted with several volumes of pentane
  3. filtrationfiltered
  4. customto remove undissolved solids which
  5. concentrationThe organics were concentrated
  6. custompurified by column chromatography (4→8% ethyl acetate/hexanes)
  7. customto give 159 mg (82%) as a colorless oil

Sources & evidence

ORD record
ord-7b901f43ce9b43c092877400d1985319
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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