Boron tribromide → 1,2-bis(3-hydroxyphenyl)ethane

HRID 46012Notes

Reaction equation

HRID 46012 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21]C)[CH:16]=2)[CH:10]=[CH:11][CH:12]=1>C(Cl)Cl>[OH:6][C:7]1[CH:8]=[C:9]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=2)[CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 434547336707-27-4

Product 1

HCID 45351801,2-bis(3-hydroxyphenyl)ethaneYield 100.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BBr3 (11.3 g, 45 mmol) was added to a solution of 1,2-bis(3-methoxyphenyl)ethane (Brunner et al., Inorg. Chim. Acta 2003, 350:39-48; 11.56 g; 47.8 mmol) in CH2Cl2 at −78° C. The reaction mixture was slowly warmed to room temperature, and stirred overnight. The reaction mixture was quenched with water, diluted with CH2Cl2, and the reaction mixture extracted with 2 M solution of NaOH (3×100 mL). The aqueous layer was slowly acidified at 0° C. with concentrated HCl to approximately pH=1, the grey precipitate was filtered, washed with water, dried in the air at room temperature, and then under vacuum at 85° C. over 5 hours to provide 10.3 g of crude 1,2-bis(3-hydroxyphenyl)ethane as grey solid.

Workup

  1. customThe reaction mixture was quenched with water
  2. additiondiluted with CH2Cl2
  3. extractionthe reaction mixture extracted with 2 M solution of NaOH (3×100 mL)
  4. customwas slowly acidified at 0° C. with concentrated HCl to approximately pH=1
  5. filtrationthe grey precipitate was filtered
  6. washwashed with water
  7. customdried in the air at room temperature

Sources & evidence

ORD record
ord-602616aed1724be18b8c81a38599d318
Source dataset
uspto-grants-2013_09
Patent number
US08541625B2

Reaction notes

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