Carbon tetrabromide → 1-Bromohexyl-4-isobutylbenzene

HRID 1034095

Reaction equation

HRID 1034095 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11](O)[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].C(Br)(Br)(Br)[Br:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Br:19][CH:11]([C:8]1[CH:9]=[CH:10][C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])=[CH:6][CH:7]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 109334301-(4-Isobutylphenyl)hexan-1-ol

Product 1

HCID 109353641-Bromohexyl-4-isobutylbenzeneYield 30.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4-isobutylphenyl)hexan-1-ol (9.15 g) and carbon tetrabromide (25.9 g) in tetrahydrofuran (250 ml) was added triphenylphosphine (20.5 g). The mixture was stirred at room temperature for 6 hours. After the white solid was filtered off, the filtrate was evaporated. n-Hexane (300 ml) was added to the residue and the precipitate was filtered off. The filtrate was evaporated and the residual oil was distilled under reduced pressure to give 1-(1-bromohexyl)-4-isobutylbenzene (3.52 g) as a colorless oil.

Workup

  1. filtrationAfter the white solid was filtered off
  2. customthe filtrate was evaporated
  3. additionn-Hexane (300 ml) was added to the residue
  4. filtrationthe precipitate was filtered off
  5. customThe filtrate was evaporated
  6. distillationthe residual oil was distilled under reduced pressure

Sources & evidence

ORD record
ord-d792b0224af74f89ba87d379767e5a0c
Source dataset
uspto-grants-1994_05
Patent number
US05312829

Linked notes

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