Water → HCID 22105598, compound

HRID 1455958Notes

Reaction equation

HRID 1455958 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][C:10]=1[CH:11]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:18]1COCC1.C[Mg]Br.O>C(OCC)C>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][C:10]=1[CH:11]([OH:12])[CH3:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 7330872-(Benzyloxy)-5-bromobenzaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 22105598HCID 22105598, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

2-Benzyloxy-5-bromobenzaldehyde (5 g) was dissolved in anhydrous diethyl ether (20 mL) and THF (20 mL) and stirred at ambient temperature under argon while a solution of methyl magnesium bromide in ether (7.4 mL, 3M solution in ether) was added dropwise over 5 minutes. A white precipitate formed. After 30 minutes the mixture was poured onto a mixture of ice and water (300 mL). The aqueous mixture was extracted with ethyl acetate (3×250 mL), the organic extracts were washed with brine (100 mL) and dried (MgSO4). After removal of the solvent the residual pale yellow oil was purified by MPLC (eluting with dichloromethane on silica) to give 1-(2-benzyloxy-5-bromophenyl)-ethanol, (5.19 g, mp 76.7° C.).

Workup

  1. additionwas added dropwise over 5 minutes
  2. customA white precipitate formed
  3. extractionThe aqueous mixture was extracted with ethyl acetate (3×250 mL)
  4. washthe organic extracts were washed with brine (100 mL)
  5. dry with materialdried (MgSO4)
  6. customAfter removal of the solvent the residual pale yellow oil
  7. customwas purified by MPLC (eluting with dichloromethane on silica)

Sources & evidence

ORD record
ord-4463d52783e7412ba2cf81a2674f9efd
Source dataset
uspto-grants-1998_12
Patent number
US05843942

Reaction notes

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