Water → HCID 19930273, compound

HRID 22435Notes

Reaction equation

HRID 22435 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][Br:21])=[CH:9][CH:8]=1.O>ClCCl>[OH:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][Br:21])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 18470410HCID 18470410, compound

Product 1

HCID 19930273HCID 19930273, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 1M solution of boron tribromide in dichloromethane (5 ml, 5 mmol) was added to an ice water cooled solution of 8-(4-methoxyphenyl)octylbromide (1.5 g, 5 mmol) in dichloromethane (10 ml). After 4 hours at room temperature, water was added and the dichloromethane separated, washed with water, dried over anhydrous magnesium sulphate, and evaporated to give an oil, which was chromatographed over flash silica, eluting with chloroform, followed by 2% methanol in chloroform to give 8-(4-hydroxyphenyl)octylbromide as an oil (MS: M+ =284).

Workup

  1. customthe dichloromethane separated
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulphate
  4. customevaporated
  5. customto give an oil, which
  6. customwas chromatographed over flash silica
  7. washeluting with chloroform

Sources & evidence

ORD record
ord-887929dd97434fdeb38adfb0c5a6fa52
Source dataset
uspto-grants-1995_06
Patent number
US05428065

Reaction notes

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