Boron tribromide → HCID 22987403, compound

HRID 986890Notes

Reaction equation

HRID 986890 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:11][CH:10]=2)[C:6]([O:20]C)=[CH:5][C:4]=1[C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:24][CH:23]=1.B(Br)(Br)Br>ClCCl>[CH2:28]([C:25]1[CH:24]=[CH:23][C:22]([C:4]2[C:3]([OH:2])=[CH:8][C:7]([C:9]3[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:13][CH:14]=3)=[C:6]([OH:20])[CH:5]=2)=[CH:27][CH:26]=1)[CH2:29][CH2:30][CH2:31][CH3:32]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22987407HCID 22987407, compound

Product 1

HCID 22987403HCID 22987403, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2′,5′-dimethoxy-4,4″-dipentyl[1,1′;4′,1″]terphenyl (2.15 g) in dichloromethane (40 ml) is cooled to −76° C. and treated with a dropwise addition of 1 M solution of boron tribromide in CH2Cl2 (12 ml). After complete addition the reaction mixture is allowed to reach room temperature and stirring is continued for 6 hours. The reaction mixture is then carefully poured into ice-water (100 g) and stirred for further 20 min. The obtained mixture is then saturated with NaCl and extracted with diethyl ether (3×150 ml). The combined organic extracts are washed with saturated NaCl solution (150 ml), dried over magnesium sulphate and evaporated under reduced pressure to afford 4,4″-dipentyl[1,1′;4′,1″]terphenyl-2′,5′-diol as white crystalline material.

Workup

  1. additionAfter complete addition the reaction mixture
  2. customto reach room temperature
  3. stirringstirred for further 20 min
  4. extractionsaturated with NaCl and extracted with diethyl ether (3×150 ml)
  5. washThe combined organic extracts are washed with saturated NaCl solution (150 ml)
  6. dry with materialdried over magnesium sulphate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-5d13340a79a24ceea76cd8225839a5e7
Source dataset
uspto-grants-2003_10
Patent number
US06630076B1

Reaction notes

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