Phosphine, triphenyl-, hydrobromide → (5-Methyl-2-thenyl)triphenylphosphonium bromide

HRID 460952

Reaction equation

HRID 460952 reaction equation
O[CH2:2][C:3]1[S:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[Br-:9].[C:10]1([PH+:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(#N)C>[Br-:9].[CH3:8][C:5]1[S:4][C:3]([CH2:2][P+:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 517696Phosphine, triphenyl-, hydrobromideHCID 528074(5-Methylthiophen-2-yl)methanol

Product 1

HCID 20285738(5-Methyl-2-thenyl)triphenylphosphonium bromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

2-Hydroxymethyl-5-methyl-thiophene (4.6 g.) was dissolved in 100 ml. of acetonitrile and 12.2 g. of triphenylphosphonium bromide were added. The reaction mixture was heated to 75° C. for 2.5 hours. After cooling the resulting precipitate was filtered off, washed with benzene and dried at 80° C. under high vacuum. The resulting (5-methyl-2-thenyl)triphenylphosphonium bromide has a m.p. 262°-266° C.

Workup

  1. temperatureAfter cooling the resulting precipitate
  2. filtrationwas filtered off
  3. washwashed with benzene
  4. customdried at 80° C. under high vacuum

Sources & evidence

ORD record
ord-66db4291badd4186acb3f122af600b68
Source dataset
uspto-grants-1977_12
Patent number
US04061656

Linked notes

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