Boron tribromide → HCID 20087288, compound

HRID 275223Notes

Reaction equation

HRID 275223 reaction equation
B(Br)(Br)Br.C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[N:17][C:18]([C:21]3[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:23][CH:22]=3)=[N:19][CH:20]=2)=[CH:11][CH:10]=1)(C)C>ClCCl>[CH2:27]([C:24]1[CH:23]=[CH:22][C:21]([C:18]2[N:17]=[CH:16][C:15]([C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=3)=[CH:20][N:19]=2)=[CH:26][CH:25]=1)[CH2:28][CH2:29][CH2:30][CH3:31]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 20087267HCID 20087267, compound

Product 1

HCID 20087288HCID 20087288, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5.5 g of boron tribromide in 50 ml of absolute dichloromethane is treated dropwise at 0° C. with a solution of 6.5 g of 5-(4-isopropyloxyphenyl)-2-(4-pentylphenyl)pyrimidine in 50 ml of absolute dichloromethane. The mixture is stirred for 24 hours and then poured on to ice-water. The organic phase is separated and the aqueous phase is back-extracted three times with 50 ml of dichloromethane each time. The combined organic phases are washed with 50 ml of 2N sodium carbonate solution and several times with water, dried over magnesium sulphate and concentrated. Chromatography of the residue on silica gel with dichloromethane/methanol (vol. 99:1) and recrystallization from hexane give 5.2 g of 4-(2-[4-pentylphenyl]-5-pyrimidinyl)phenol with m.p. 152°-153° C.

Workup

  1. customThe organic phase is separated
  2. extractionthe aqueous phase is back-extracted three times with 50 ml of dichloromethane each time
  3. washThe combined organic phases are washed with 50 ml of 2N sodium carbonate solution and several times with water
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated
  6. customChromatography of the residue on silica gel with dichloromethane/methanol (vol. 99:1) and recrystallization from hexane

Sources & evidence

ORD record
ord-bd66b251ee1041cba5da12f8272f493c
Source dataset
uspto-grants-1995_02
Patent number
US05393458

Reaction notes

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