Carbon tetrabromide → HCID 178444252, compound

HRID 1380781Notes

Reaction equation

HRID 1380781 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21](CO)=[CH:20][CH:19]=3)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:46]([Br:49])(Br)Br>C(Cl)Cl>[Br:49][CH2:46][C:21]1[CH:22]=[CH:23][C:18]([C:15]2[CH:14]=[CH:13][C:12]([C@H:9]3[CH2:10][CH2:11][C@H:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:7][CH2:8]3)=[CH:17][CH:16]=2)=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 178444272HCID 178444272, compound

Product 1

HCID 178444252HCID 178444252, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3.5 g of 4'-(trans-4-pentylcyclohexyl)-4-biphenylmethanol and 2.9 g of triphenylphosphine in 150 ml of absolute methylene chloride was placed at -20° C. in a sulphonation flask while gassing with argon and treated portionwise within 10 minutes with 3.8 g of solid tetrabromomethane. Partially undissolved educt thereby dissolved slowly. The mixture was stirred for a further 2 hours while warming to room temperature. The mixture was subsequently concentrated on a rotary evaporator and the crystalline residue was suspended in 300 ml of warm hexane, freed by filtration from precipitated triphenylphosphine oxide (rinsing with hexane) and the filtrate was concentrated. Low-pressure chromatography (0.7 bar) of the residue on silica gel with toluene as the eluant gave 3.39 g (82%) of 4-(bromomethyl)-4'-(trans-4-pentylcyclohexyl)biphenyl as colourless crystals. This material was used in the following step without further purification. Rf value of the product [petroleum ether/ethyl acetate (97:3)]: 0.47.

Workup

  1. customwas placed at -20° C. in a sulphonation flask
  2. dissolutionPartially undissolved educt thereby dissolved slowly
  3. concentrationThe mixture was subsequently concentrated on a rotary evaporator
  4. filtrationfreed by filtration
  5. customfrom precipitated triphenylphosphine oxide (rinsing with hexane)
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-2f2a15bf34dc4478a56b825ec30d4fe3
Source dataset
uspto-grants-1986_04
Patent number
US04583826

Reaction notes

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