Carbon tetrabromide → HCID 12138359, compound

HRID 1271669Notes

Reaction equation

HRID 1271669 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:34]=[C:35]([C:37]([CH3:40])([CH3:39])[CH3:38])[CH:36]=1)[CH2:8][S:9][C:10]1[CH:11]=[C:12]([CH:15]=[C:16]([S:18][CH2:19][C:20]2[CH:25]=[C:24]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:23]=[C:22]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:21]=2)[CH:17]=1)[CH2:13]O)([CH3:4])([CH3:3])[CH3:2].C(Br)(Br)(Br)[Br:42].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:1]([C:5]1[CH:6]=[C:7]([CH:34]=[C:35]([C:37]([CH3:40])([CH3:39])[CH3:38])[CH:36]=1)[CH2:8][S:9][C:10]1[CH:11]=[C:12]([CH:15]=[C:16]([S:18][CH2:19][C:20]2[CH:25]=[C:24]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:23]=[C:22]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:21]=2)[CH:17]=1)[CH2:13][Br:42])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 12138358HCID 12138358, compound

Product 1

HCID 12138359HCID 12138359, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3,5-Bis(3,5-di-tertiary-butylbenzylthio)benzyl alcohol (49.0 g, 84.9 mmol) and carbon tetrabromide (28.2 g, 85.0 mmol) were dissolved in 300 ml of tetrahydrofuran. To this solution was added with stirring triphenylphosphin (23.5 g, 89.6 mmol), at the temperatures of 10° C. or below. The reaction mixture became clear once, and then colorless crystals separated gradually. After stirring overnight at 25–30° C., the crystals were removed by filtration and the filtrate was concentrated. The residue obtained was purified by means of chromatography with n-hexane:dichloromethane=1:1, giving 34.8 g of 3,5-bis(3,5-di-tertiary-butylbenzylthio)benzyl bromide.

Workup

  1. customcolorless crystals separated gradually
  2. customthe crystals were removed by filtration
  3. concentrationthe filtrate was concentrated
  4. customThe residue obtained
  5. customwas purified by means of chromatography with n-hexane

Sources & evidence

ORD record
ord-455ff5c9c50f470ba3fb644976b24a50
Source dataset
uspto-grants-2007_04
Patent number
US07205428B2

Reaction notes

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